Liquid crystal display device

ABSTRACT

The present invention relates to a liquid crystal display device including a specific liquid crystal composition and a sealant in which a cured product of a specific curable resin composition is used. 
     The present invention provides a liquid crystal display device which prevents a decrease in the voltage holding ratio (VHR) of the liquid crystal layer and which enables elimination of problematic defective display such as voids, uneven alignment, and screen burn-in. 
     Since the liquid crystal display device of the present invention prevents a decrease in the voltage holding ratio (VHR) of the liquid crystal layer and enables a reduction in defective display such as uneven alignment and screen burn-in, it is particularly useful for active-matrix liquid crystal display devices of a VA mode and PSVA mode and can be applied to liquid crystal display apparatuses such as liquid crystal TVs, monitors, mobile phones, and smartphones.

TECHNICAL FIELD

The present invention relates to a liquid crystal display device.

BACKGROUND ART

Liquid crystal display devices have been applied to, for example,watches, calculators, a variety of household electrical appliances,measuring equipment, panels used in automobiles, word processors,electronic notebooks, printers, computers, and television sets.Representative examples of types of liquid crystal display devicesinclude a TN (twisted nematic) type, an STN (super twisted nematic)type, a DS (dynamic scattering) type, a GH (guest•host) type, an IPS(in-plane switching) type, an OCB (optically compensated birefringence)type, an ECB (electrically controlled birefringence) type, a VA(vertical alignment) type, a CSH (color super homeotropic) type, and anFLC (ferroelectric liquid crystal) type. Regarding a drive system,multiplex driving has become popular instead of typical static driving;a passive matrix, in particular, an active matrix (AM) in which, forexample, a TFT (thin film transistor) or TFD (thin film diode) is usedhas become mainstream in recent years.

In a method for manufacturing liquid crystal display devices, a droppingtechnique involving use of an optically and thermally curable sealant iswidely used. In the dropping technique, a rectangular sealing pattern isformed on one of two transparent substrates each having an electrode byusing a dispenser or by screen printing. Then, fine droplets of liquidcrystal are dropped onto the entire surface of the transparent substrateinside the frame in a state in which the sealant has not been cured yet,this transparent substrate is immediately attached to the othertransparent substrate, and then the sealing part is irradiated withultraviolet to be temporarily cured. Then, the sealant is completelycured by heating at the time of liquid crystal annealing to produce aliquid crystal display device. Attaching the substrates to each otherunder reduced pressure enables production of liquid crystal displaydevices with significantly high efficiency.

Since the dropping technique has a process in which an uncured sealantdirectly contacts liquid crystal material, the liquid crystal materialis contaminated by a component of the sealant, which has been greatlyproblematic. In addition, residues, such as an unreacted polymerizationinitiator and a curing agent, and ionic impurities contained in a curedsealant have been also problematic. These days, in liquid crystalpanels, liquid crystal driven at low voltage (low-voltage liquidcrystal) tends to be used for the purpose of a reduction in powerconsumption, for instance, in application to mobile devices. Suchlow-voltage liquid crystal has a particularly large dielectricanisotropy and therefore easily takes in impurities, which readilyresults in defective alignment and a reduction in a voltage holdingratio over time. In particular, residues, such as an unreactedpolymerization initiator and an initiator used for curing, ionicimpurities such as chlorine, or silane coupling agents contained in asealant flow into a liquid crystal material, and thus problems such asdefective alignment and a reduction in a voltage holding ratio over timeare caused.

In such circumstances, in order to prevent a component of a sealant fromflowing into a liquid crystal material, there has been a suggestion inwhich the softening point of an epoxy resin contained in the sealant isenhanced for prevention of contamination of the liquid crystal materialdue to contact thereof with an uncured sealant and for a reduction incolor unevenness (Patent Literature 1). Another suggestion forpreventing a component of a sealant from flowing has been suggested; thesealant having a composition which enables both optical curing andthermal curing is prepared, the sealant is applied and then temporarilycured by being irradiated with light in order to avoid contaminationbrought about by contact thereof with a liquid crystal material, twosubstrates are attached to each other, and then the sealant iscompletely cured by heating (Patent Literature 2). In order to enablethis suggestion, an acrylic-acid-modified epoxy resin produced by thereaction of an epoxy resin with acrylic acid is used as a component ofthe sealant.

In general, epoxy resins have a high adhesiveness but greatly tend tocontaminate liquid crystal materials. It is expected that theabove-mentioned modification with acrylic acid also contributes to areduction in contamination of liquid crystal materials. The modificationwith acrylic acid, however, impairs thermosetting properties, whichresults in contamination of a liquid crystal material due to flowing ofa component of the sealant thereinto in some cases. Another suggestionhas been therefore made in order to cure an acrylic component; atertiary amine such as imidazole is added to thermally cure an acrylicresin owing to the interaction thereof with a small amount of an epoxyresin which has been also added (Patent Literature 3).

In each of the suggestions, however, liquid crystal materials generallyused are considered, attention is paid to the composition of thesealant, and a change is made to the composition of the sealant with theaim of solving the problems. Hence, in the case where such suggestionsare applied to individual liquid crystal display devices, the liquidcrystal display devices do not necessarily have sufficient displayproperties in many cases; in particular, the screen burn-in of a liquidcrystal display device has not been sufficiently overcome.

CITATION LIST Patent Literature

PTL 1: Japanese Unexamined Patent Application Publication No. 2006-23582

PTL 2: Japanese Unexamined Patent Application Publication No. 2005-18022

PTL 3: Japanese Unexamined Patent Application Publication No.2008-116825

SUMMARY OF INVENTION Technical Problem

In the present invention, the interaction of the components of a liquidcrystal material with a sealant is considered even though attention hastypically not been paid so much thereto, and a combination of thecomposition of liquid crystal and the composition of a sealant for animprovement in the defective display of liquid crystal display devices,such as screen burn-in, is proposed.

In particular, it is an object of the present invention to provide aliquid crystal display device in which a specific liquid crystalcomposition and a sealant which is the cured product of a specificcurable resin composition are used; use of such a liquid crystalcomposition and sealant gives a practical temperature range of a liquidcrystal phase, dielectric anisotropy (Δ∈) with a large absolute value,low viscosity, and proper refractive index anisotropy (Δn), prevents adecrease in the voltage holding ratio (VHR) of the liquid crystal layer,and eliminates problematic defective display such as voids, unevenalignment, and screen burn-in.

Solution to Problem

The inventors have intensively studied a combination of the structure ofa curable resin composition contained in a sealant and the structure ofa liquid crystal material used in a liquid crystal layer in order toachieve such an object and found that using a liquid crystal materialhaving a specific structure and a sealant containing the cured productof a specific curable resin composition in a liquid crystal displaydevice prevents a decrease in the voltage holding ratio (VHR) of theliquid crystal layer and eliminates problematic defective display suchas voids, uneven alignment, and screen burn-in, thereby accomplishingthe present invention.

In particular, the present invention provides a liquid crystal displaydevice including a first substrate, a second substrate, a liquid crystallayer containing a liquid crystal composition and disposed between thefirst and second substrates, and a sealant which is a cured product of acurable resin composition which is cured by being exposed to an energyray or heat, the first and second substrates being attached to eachother by the sealant, wherein the liquid crystal composition contains 30to 50% of a compound represented by General Formula (I)

(where R¹ and R² each independently represent an alkyl group having 1 to8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxygroup having 1 to 8 carbon atoms, or an alkenyloxy group having 2 to 8carbon atoms; and A represents a 1,4-phenylene group or atrans-1,4-cyclohexylene group), 5 to 30% of a compound represented byGeneral Formula (II-1)

(where R³ represents an alkyl group having 1 to 8 carbon atoms, analkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms; R⁴represents an alkyl group having 1 to 8 carbon atoms, an alkenyl grouphaving 4 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms,or an alkenyloxy group having 3 to 8 carbon atoms; and Z³ represents asingle bond, —CH═CH—, —C≡C—, —CH₂CH₂—, —(CH₂)₄—, —COO—, —OCO—, —OCH₂—,—CH₂O—, —OCF₂—, or —CF₂O—), and 25 to 45% of a compound represented byGeneral Formula (II-2)

(where R⁵ represents an alkyl group having 1 to 8 carbon atoms, analkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms; R⁶represents an alkyl group having 1 to 8 carbon atoms, an alkenyl grouphaving 4 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms,or an alkenyloxy group having 3 to 8 carbon atoms; B represents a1,4-phenylene group or trans-1,4-cyclohexylene group which is optionallysubstituted with a fluorine atom; Z⁴ represents a single bond, —CH═CH—,—C≡C—, —CH₂CH₂—, —(CH₂)₄—, —COO—, —OCO—, —OCH₂—, —CH₂O—, —OCF₂—, or—CF₂O—); and the curable resin composition contains a compound having atleast one (meth)acrylic group and at least one epoxy group per molecule.

Advantageous Effects of Invention

In the liquid crystal display device of the present invention, using aspecific liquid crystal composition and a sealant containing the curedproduct of a specific curable resin composition can give a practicaltemperature range of a liquid crystal layer, dielectric anisotropy (Δ∈)with a large absolute value, low viscosity, and proper refractive indexanisotropy (Δn); prevent a decrease in the voltage holding ratio (VHR)of the liquid crystal layer; and eliminate defective display such asvoids, uneven alignment, and screen burn-in.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a plan view illustrating a liquid crystal display device ofthe present invention.

FIG. 2 is an enlarged view illustrating the liquid crystal displaydevice of the present invention.

REFERENCE SIGNS LIST

1 Substrate

2 Sealant

3 Liquid crystal

4 Driver

5 Wires from pixel electrodes

6 Overcoat layer

7 Pixel electrode or wire

8 Alignment film

DESCRIPTION OF EMBODIMENTS

FIG. 1 is a plan view illustrating the liquid crystal display device ofthe present invention. The details of pixel electrodes, TFTs, wires, andanother component are omitted. The upper part of FIG. 2 is an enlargedpartial view illustrating part of the plan view, in which wires extendfrom corresponding pixel electrodes to a driver and are positioned belowa sealant. The lower part of FIG. 2 is a cross-sectional viewillustrating the liquid crystal display device in the upper part of FIG.2. The sealant contacts liquid crystal and an alignment film. Dependingon a position at which the sealant is disposed, the sealant or liquidcrystal may contact wires or an overcoat layer although it is not shownin the drawing.

(Liquid Crystal Layer)

The liquid crystal layer of the liquid crystal display device of thepresent invention contains a liquid crystal composition containing 30 to50% of a compound represented by General Formula (I)

(where R¹ and R² each independently represent an alkyl group having 1 to8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxygroup having 1 to 8 carbon atoms, or an alkenyloxy group having 2 to 8carbon atoms; and A represents a 1,4-phenylene group or atrans-1,4-cyclohexylene group), 5 to 30% of a compound represented byGeneral Formula (II-1)

(where R³ represents an alkyl group having 1 to 8 carbon atoms, analkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms; R⁴represents an alkyl group having 1 to 8 carbon atoms, an alkenyl grouphaving 4 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms,or an alkenyloxy group having 3 to 8 carbon atoms; and Z³ represents asingle bond, —CH═CH—, —C≡C—, —CH₂CH₂—, —(CH₂)₄—, —COO—, —OCO—, —OCH₂—,—CH₂O—, —OCF₂—, or —CF₂O—), and 25 to 45% of a compound represented byGeneral Formula (II-2).

(where R⁵ represents an alkyl group having 1 to 8 carbon atoms, analkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms; R⁶represents an alkyl group having 1 to 8 carbon atoms, an alkenyl grouphaving 4 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms,or an alkenyloxy group having 3 to 8 carbon atoms; B represents a1,4-phenylene group or trans-1,4-cyclohexylene group which is optionallysubstituted with a fluorine atom; and Z⁴ represents a single bond,—CH═CH—, —C≡C—, —CH₂CH₂—, —(CH₂)₄—, —COO—, —OCO—, —OCH₂—, —CH₂O—,—OCF₂—, or —CF₂O—).

The liquid crystal layer of the liquid crystal display device of thepresent invention contains 30 to 50% of the compound represented byGeneral Formula (I), preferably 32 to 48%, and more preferably 34 to46%.

In General Formula (I), R¹ and R² each independently represent an alkylgroup having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbonatoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyloxygroup having 2 to 8 carbon atoms. In the case where A represents atrans-1,4-cyclohexylene group,

-   R¹ and R² preferably each independently represent an alkyl group    having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon    atoms, an alkoxy group having 1 to 5 carbon atoms, or an alkenyloxy    group having 2 to 5 carbon atoms, more preferably an alkyl group    having 2 to 5 carbon atoms, an alkenyl group having 2 to 4 carbon    atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyloxy    group having 2 to 4 carbon atoms; and-   R¹ preferably represents an alkyl group; in this case, an alkyl    group having 2, 3, or 4 carbon atoms is especially preferred. In the    case where R¹ represents an alkyl group having 3 carbon atoms, R² is    preferably an alkyl group having 2, 4, or 5 carbon atoms or an    alkenyl group having 2 or 3 carbon atoms; and more preferably an    alkyl group having 2 carbon atoms.-   In the case where A represents a 1,4-phenylene group, R¹ and R²    preferably each independently represent an alkyl group having 1 to 5    carbon atoms, an alkenyl group having 4 or 5 carbon atoms, an alkoxy    group having 1 to 5 carbon atoms, or an alkenyloxy group having 3 to    5 carbon atoms, more preferably an alkyl group having 2 to 5 carbon    atoms, an alkenyl group having 4 or 5 carbon atoms, an alkoxy group    having 1 to 4 carbon atoms, or an alkenyloxy group having 2 to 4    carbon atoms; and-   R¹ preferably represents an alkyl group; in this case, an alkyl    group having 1, 3, or 5 carbon atoms is especially preferred. R²    preferably represents an alkoxy group having 1 or 2 carbon atoms.

The amount of a compound represented by General Formula (I) in which atleast any one of the substituents R¹ and R² is an alkyl group having 3to 5 carbon atoms is preferably not less than 50%, more preferably notless than 70%, and further preferably not less than 80% relative to thetotal amount of compounds represented by General Formula (I). The amountof a compound represented by General Formula (I) in which at least anyone of the substituents R¹ and R² is an alkyl group having 3 carbonatoms is preferably not less than 50%, more preferably not less than70%, further preferably not less than 80%, and most preferably 100%relative to the total amount of compounds represented by General Formula(I).

One or more compounds represented by General Formula (I) can be used; itis preferred that at least one compound in which A represents atrans-1,4-cyclohexylene group and at least one compound in which Arepresents a 1,4-phenylene group be used.

The amount of the compound represented by General Formula (I) in which Arepresents a trans-1,4-cyclohexylene group is preferably not less than50%, more preferably not less than 70%, and further preferably not lessthan 80% relative to the total amount of compounds represented byGeneral Formula (I).

In particular, the compound represented by General Formula (I) ispreferably any of compounds represented by General Formulae (Ia) to(Ik).

(where R¹ and R² each independently represent an alkyl group having 1 to5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms butpreferably have the same meaning as R¹ and R² in General Formula (I),respectively) Among General Formulae (Ia) to (Ik), General Formulae(Ia), (Ic), and (Ig) are preferred; General Formulae (Ia) and (Ig) aremore preferred; and General Formula (Ia) is especially preferred. In thecase of focusing on a response speed, General Formula (Ib) is alsopreferred; in the case of further focusing on a response speed, GeneralFormulae (Ib), (Ic), (Ie), and (Ik) are preferred, and General Formulae(Ic) and (Ik) are more preferred. Dialkenyl compounds represented byGeneral Formula (Ik) are especially preferred in the case of especiallyfocusing on a response speed.

From this viewpoint, the amount of compounds represented by GeneralFormulae (Ia) and (Ic) is preferably not less than 50%, more preferablynot less than 70%, further preferably not less than 80%, and mostpreferably 100% relative to the total amount of compounds represented byGeneral Formula (I). The amount of a compound represented by GeneralFormula (Ia) is preferably not less than 50%, more preferably not lessthan 70%, and further preferably not less than 80% relative to the totalamount of compounds represented by General Formula (I).

The liquid crystal layer of the liquid crystal display device of thepresent invention contains 5 to 30% of the compound represented byGeneral Formula (II-1), preferably 8 to 27%, and more preferably 10 to25%.

In General Formula (II-1), R³ represents an alkyl group having 1 to 8carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxygroup having 1 to 8 carbon atoms, or an alkenyloxy group having 2 to 8carbon atoms; preferably an alkyl group having 1 to 5 carbon atoms or analkenyl group having 2 to 5 carbon atoms; more preferably an alkyl grouphaving 2 to 5 carbon atoms or an alkenyl group having 2 to 4 carbonatoms; further preferably an alkyl group having 3 to 5 carbon atoms oran alkenyl group having 2 carbon atoms; and especially preferably analkyl group having 3 carbon atoms.

R⁴ represents an alkyl group having 1 to 8 carbon atoms, an alkenylgroup having 4 to 8 carbon atoms, an alkoxy group having 1 to 8 carbonatoms, or an alkenyloxy group having 3 to 8 carbon atoms; preferably analkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5carbon atoms; more preferably an alkyl group having 1 to 3 carbon atomsor an alkoxy group having 1 to 3 carbon atoms; further preferably analkyl group having 3 carbon atoms or an alkoxy group having 2 carbonatoms; and especially preferably an alkoxy group having 2 carbon atoms.

Z³ represents a single bond, —CH═CH—, —C≡C—, —CH₂CH₂—, —(CH₂)₄—, —COO—,—OCO—, —OCH₂—, —CH₂O—, —OCF₂—, or —CF₂O—; preferably a single bond,—CH₂CH₂—, —COO—, —OCH₂—, —CH₂O—, —OCF₂—, or —CF₂O—; and more preferablya single bond or —CH₂O—.

The liquid crystal layer of the liquid crystal display device of thepresent invention can contain at least one compound represented byGeneral Formula (II-1) and preferably contains one or two compoundsrepresented by General Formula (II-1).

In particular, the compound represented by General Formula (II-1) ispreferably any of compounds represented by General Formulae (II-1a) to(II-1d).

(where R³ represents an alkyl group having 1 to 5 carbon atoms or analkenyl group having 2 to 5 carbon atoms; R^(4a) represents an alkylgroup having 1 to 5 carbon atoms)

In General Formulae (II-1a) and (II-1c), R³ preferably has the samemeaning as R³ in General Formula (II-1). R^(4a) preferably represents analkyl group having 1 to 3 carbon atoms, more preferably an alkyl grouphaving 1 or 2 carbon atoms, and especially preferably an alkyl grouphaving 2 carbon atoms.

In General Formulae (II-1b) and (II-1d), R³ preferably has the samemeaning as R³ in General Formula (II-1). R^(4a) preferably represents analkyl group having 1 to 3 carbon atoms, more preferably an alkyl grouphaving 1 or 3 carbon atoms, and especially preferably an alkyl grouphaving 3 carbon atoms.

Among General Formulae (II-1a) to (II-1d), in order to increase theabsolute value of dielectric anisotropy, General Formulae (II-1a) and(II-1c) are preferred, and General Formula (II-1a) is more preferred.

The liquid crystal layer of the liquid crystal display device of thepresent invention preferably contains at least one of compoundsrepresented by General Formulae (II-1a) to (II-1d), also preferably oneor two of them, and also preferably one or two of compounds representedby General Formula (II-1a).

The liquid crystal layer of the liquid crystal display device of thepresent invention contains 25 to 45% of a compound represented byGeneral Formula (II-2), preferably 28 to 42%, and more preferably 30 to40%.

In General Formula (II-2), R⁵ represents an alkyl group having 1 to 8carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxygroup having 1 to 8 carbon atoms, or an alkenyloxy group having 2 to 8carbon atoms; preferably an alkyl group having 1 to 5 carbon atoms or analkenyl group having 2 to 5 carbon atoms; more preferably an alkyl grouphaving 2 to 5 carbon atoms or an alkenyl group having 2 to 4 carbonatoms; further preferably an alkyl group having 3 to 5 carbon atoms oran alkenyl group having 2 carbon atoms; and especially preferably analkyl group having 3 carbon atoms.

R⁶ represents an alkyl group having 1 to 8 carbon atoms, an alkenylgroup having 4 to 8 carbon atoms, an alkoxy group having 1 to 8 carbonatoms, or an alkenyloxy group having 3 to 8 carbon atoms; preferably analkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5carbon atoms; more preferably an alkyl group having 1 to 3 carbon atomsor an alkoxy group having 1 to 3 carbon atoms; further preferably analkyl group having 3 carbon atoms or an alkoxy group having 2 carbonatoms: and especially preferably an alkoxy group having 2 carbon atoms.

B represents a 1,4-phenylene group or trans-1,4-cyclohexylene groupwhich is optionally substituted with a fluorine atom, preferably anunsubstituted 1,4-phenylene group or trans-1,4-cyclohexylene group, andmore preferably the trans-1,4-cyclohexylene group.

Z⁴ represents a single bond, —CH═CH—, —C≡C—, —CH₂CH₂—, —(CH₂)₄—, —COO—,—OCO—, —OCH₂—, —CH₂O —, —OCF₂—, or —CF₂O—; preferably a single bond,—CH₂CH₂—, —COO—, —OCH₂—, —CH₂O—, —OCF₂—, or —CF₂O—; and more preferablya single bond or —CH₂O—.

In particular, the compound represented by General Formula (II-2) ispreferably any of compounds represented by General Formulae (II-2a) to(II-2f).

(where R⁵ represents an alkyl group having 1 to 5 carbon atoms or analkenyl group having 2 to 5 carbon atoms, and R^(6a) represents an alkylgroup having 1 to 5 carbon atoms; R⁵ and R^(6a) preferably have the samemeanings as R⁵ and R⁶ in General Formula (II-2), respectively)

In General Formulae (II-2a), (II-2b), and (II-2e), R⁵ preferably has thesame meaning as R⁵ in General Formula (II-2). R^(6a) is preferably analkyl group having 1 to 3 carbon atoms, more preferably an alkyl grouphaving 1 or 2 carbon atoms, or especially preferably an alkyl grouphaving 2 carbon atoms.

In General Formulae (II-2c), (II-2d), and (II-2f), R⁵ preferably has thesame meaning as R⁵ in General Formula (II-2). R^(6a) is preferably analkyl group having 1 to 3 carbon atoms, more preferably an alkyl grouphaving 1 or 3 carbon atoms, or especially preferably an alkyl grouphaving 3 carbon atoms.

Among General Formulae (II-2a) to (II-2f), in order to increase theabsolute value of dielectric anisotropy, General Formulae (II-2a),(II-2b), and (II-2e) are preferred.

At least one compound represented by General Formula (II-2) can be used;it is preferred that at least one compound in which B represents a1,4-phenylene group and at least one compound in which B represents atrans-1,4-cyclohexylene group be used.

The liquid crystal layer of the liquid crystal display device of thepresent invention preferably further contains a compound represented byGeneral Formula (III).

(where R⁷ and R⁸ each independently represent an alkyl group having 1 to8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxygroup having 1 to 8 carbon atoms, or an alkenyloxy group having 2 to 8carbon atoms; D, E, and F each independently represent a 1,4-phenylenegroup or trans-1,4-cyclohexylene which is optionally substituted with afluorine atom; Z² represents a single bond, —OCH₂—, —OCO—, —CH₂O—,—COO—, or —OCO—; n represents 0, 1, or 2; and the compound representedby General Formula (III) excludes the compounds represented by GeneralFormulae (I), (II-1), and (II-2))

The amount of the compound represented by General Formula (III) ispreferably in the range of 3 to 35%, also preferably 5 to 33%, and alsopreferably 7 to 30%.

In General Formula (III), R⁷ represents an alkyl group having 1 to 8carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxygroup having 1 to 8 carbon atoms, or an alkenyloxy group having 2 to 8carbon atoms.

In the case where D represents trans-1,4-cyclohexylene, R⁷ preferablyrepresents an alkyl group having 1 to 5 carbon atoms or an alkenyl grouphaving 2 to 5 carbon atoms; more preferably an alkyl group having 2 to 5carbon atoms or an alkenyl group having 2 to 4 carbon atoms; furtherpreferably an alkyl group having 3 to 5 carbon atoms or an alkenyl grouphaving 2 or 3 carbon atoms; and especially preferably an alkyl grouphaving 3 carbon atoms.In the case where D represents a 1,4-phenylene group which is optionallysubstituted with a fluorine atom, R⁷ preferably represents an alkylgroup having 1 to 5 carbon atoms or an alkenyl group having 4 or 5carbon atoms, more preferably an alkyl group having 2 to 5 carbon atomsor an alkenyl group having 4 carbon atoms; and further preferably analkyl group having 2 to 4 carbon atoms.

R⁸ represents an alkyl group having 1 to 8 carbon atoms, an alkenylgroup having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbonatoms, or an alkenyloxy group having 3 to 8 carbon atoms.

In the case where F represents trans-1,4-cyclohexylene, R⁸ preferablyrepresents an alkyl group having 1 to 5 carbon atoms or an alkenyl grouphaving 2 to 5 carbon atoms; more preferably an alkyl group having 2 to 5carbon atoms or an alkenyl group having 2 to 4 carbon atoms; furtherpreferably an alkyl group having 3 to 5 carbon atoms or an alkenyl grouphaving 2 or 3 carbon atoms; and especially preferably an alkyl grouphaving 3 carbon atoms.In the case where F represents a 1,4-phenylene group which is optionallysubstituted with a fluorine atom, R⁸ preferably represents an alkylgroup having 1 to 5 carbon atoms or an alkenyl group having 4 or 5carbon atoms, more preferably an alkyl group having 2 to 5 carbon atomsor an alkenyl group having 4 carbon atoms; and further preferably analkyl group having 2 to 4 carbon atoms.

In the case where R⁷ and R⁸ each represent an alkenyl group and whereany one of D and F bonded to R⁷ and R⁸, respectively, is a 1,4-phenylenegroup which is optionally substituted with a fluorine atom, an alkenylgroup having 4 or 5 carbon atoms is preferably any of the followingstructures.

(where the right end of each of the structures is bonded to the ringstructure)Also in this case, an alkenyl group having 4 carbon atoms is morepreferred.

D, E, and F each independently represent a 1,4-phenylene group ortrans-1,4-cyclohexylene which is optionally substituted with a fluorineatom; preferably a 2-fluoro-1,4-phenylene group, a2,3-difluoro-1,4-phenylene group, a 1,4-phenylene group, ortrans-1,4-cyhclohexylene; more preferably a 2-fluoro-1,4-phenylenegroup, a 2,3-difluoro-1,4-phenylene group, or a 1,4-phenylene group;especially preferably a 2,3-difluoro-1,4-phenylene group or a1,4-phenylene group.

Z² represents a single bond, —OCH₂—, —OCO—, —CH₂O—, or —COO—; preferablya single bond, —CH₂O—, or —COO—; and more preferably a single bond.

n represents 0, 1, or 2, and preferably 0 or 1. In the case where Z²does not represent a single bond but represents a substituent, npreferably represents 1. In the case where n represents 1, the compoundrepresented by General Formula (III) is preferably any of compoundsrepresented by General Formulae (III-1a) to (III-1e) in terms of anenhancement in negative dielectric anisotropy or any of compoundsrepresented by General Formulae (III-1f) to (III-1j) in terms of anincrease in a response speed.

(where R⁷ and R⁸ each independently represent an alkyl group having 1 to5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or analkoxy group having 1 to 5 carbon atoms; R⁷ and R⁸ preferably have thesame meanings as R⁷ and R⁸ in General Formula (III), respectively)

In the case where n represents 2, the compound represented by GeneralFormula (III) is preferably any of compounds represented by GeneralFormulae (III-2a) to (III-2i) in terms of an enhancement in negativedielectric anisotropy or any of compounds represented by GeneralFormulae (III-2j) to (III-2l) in terms of an increase in a responsespeed.

(where R⁷ and R⁸ each independently represent an alkyl group having 1 to5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or analkoxy group having 1 to 5 carbon atoms; R⁷ and R⁸ preferably have thesame meanings as R⁷ and R⁸ in General Formula (III), respectively)

In the case where n represents 0, the compound represented by GeneralFormula (III) is preferably a compound represented by General Formula(III-3a) in terms of an enhancement in negative dielectric anisotropy ora compound represented by General Formula (III-3b) in terms of anincrease in a response speed.

(where R⁷ and R⁸ each independently represent an alkyl group having 1 to5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or analkoxy group having 1 to 5 carbon atoms; R⁷ and R⁸ preferably have thesame meanings as R⁷ and R⁸ in General Formula (III), respectively)

R⁷ preferably represent an alkyl group having 2 to 5 carbon atoms, andmore preferably an alkyl group having 3 carbon atoms. R⁸ preferablyrepresent an alkoxy group having 1 to 3 carbon atoms, and morepreferably an alkoxy group having 2 carbon atoms.

Each of the compounds represented by General Formulae (II-1) and (II-2)is a compound having a negative dielectric anisotropy with a relativelylarge absolute value; the total amount thereof is preferably in therange of 30 to 65%, more preferably 40 to 55%, and especially preferably43 to 50%.

The compound represented by General Formula (III) includes a compoundhaving a positive dielectric anisotropy and a compound having a negativedielectric anisotropy. In the case where a compound represented byGeneral Formula (III) and having a negative dielectric anisotropy withan absolute value of not less than 0.3 is used, the total amount ofcompounds represented by General Formulae (II-1), (II-2), and (III) ispreferably in the range of 35 to 70%, more preferably 45 to 65%, andespecially preferably 50 to 60%.

It is preferred that the amount of the compound represented by GeneralFormula (I) be in the range of 30 to 50% and that the amount of thecompounds represented by General Formulae (II-1), (II-2), and (III) bein the range of 35 to 70%; it is more preferred that the amount of thecompound represented by General Formula (I) be in the range of 35 to 45%and that the amount of the compounds represented by General Formulae(II-1), (II-2), and (III) be in the range of 45 to 65%; and it isespecially preferred that the amount of the compound represented byGeneral Formula (I) be in the range of 38 to 42% and that the amount ofthe compounds represented by General Formulae (II-1), (II-2), and (III)be in the range of 50 to 60%.

The total amount of the compounds represented by General Formulae (I),(II-1), (II-2), and (III) is preferably in the range of 80 to 100%, morepreferably 90 to 100%, and especially preferably 95 to 100% relative tothe total amount of the composition.

The liquid crystal layer of the liquid crystal display device of thepresent invention can be used in a wide range of nematic phase-isotropicliquid phase transition temperature (T_(ni)); this temperature range ispreferably from 60 to 120° C., more preferably from 70 to 100° C., andespecially preferably from 70 to 85° C.

The dielectric anisotropy is preferably in the range of −2.0 to −6.0,more preferably −2.5 to −5.0, and especially preferably −2.5 to −4.0 at25° C.

The refractive index anisotropy is preferably from 0.08 to 0.13, andmore preferably from 0.09 to 0.12 at 25° C. In particular, therefractive index anisotropy is preferably from 0.10 to 0.12 for a thincell gap or is preferably from 0.08 to 0.10 for a thick cell gap.

The rotational viscosity (γ1) is preferably not more than 150, morepreferably not more than 130, and especially preferably not more than120.

In the liquid crystal layer of the liquid crystal display device of thepresent invention, it is preferred that the function Z of the rotationalviscosity and the refractive index anisotropy have a specific value.Z=γ1/Δn ²  [Math. 1](where γ1 represents rotational viscosity, and Δn represents refractiveindex anisotropy)Z is preferably not more than 13000, more preferably not more than12000, and especially preferably not more than 11000.

In the case where the liquid crystal layer of the liquid crystal displaydevice of the present invention is used in an active-matrix displaydevice, the liquid crystal layer needs to have a specific resistance ofnot less than 10¹²(Ω·m), preferably 10¹³(Ω·m), and more preferably notless than 10¹⁴(Ω·m).

In addition to the above-mentioned compounds, the liquid crystal layerof the liquid crystal display device of the present invention maycontain, for example, general nematic liquid crystal, smectic liquidcrystal, cholesteric liquid crystal, antioxidants, ultravioletabsorbers, and polymerizable monomers, depending on application thereof.

The polymerizable monomer is preferably a difunctional monomerrepresented by General Formula (V).

(where X¹ and X² each independently represent a hydrogen atom or amethyl group;

Sp¹ and Sp² each independently represent a single bond, an alkylenegroup having 1 to 8 carbon atoms, or —O—(CH₂)_(s)— (where s representsan integer from 1 to 7, and the oxygen atom is bonded to an aromaticring);

Z¹ represents —OCH₂—, —CH₂O—, —COO—, —OCO—, —CF₂O—, —OCF₂—, —CH₂CH₂—,—CF₂CF₂—, —CH═CH—OCO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—,—COO—CH₂CH₂—, —OCO—CH₂CH₂—, —CH₂CH₂—COO—, —CH₂CH₂—OCO—, —COO—CH₂—,—OCO—CH₂—, —CH₂—COO—, —CH₂—OCO—, —CY¹═CY²— (where Y¹ and Y² eachindependently represent a fluorine atom or a hydrogen atom), —C≡C—, or asingle bond; and

C represents a 1,4-phenylene group, a trans-1,4-cyclohexylene group, ora single bond, and in each 1,4-phenylene group in the formula, anyhydrogen atom is optionally substituted with a fluorine atom)

Diacrylate derivatives in which X¹ and X² each represent a hydrogen atomand dimethacrylate derivatives in which X¹ and X² are each a methylgroup are preferred, and compounds in which one of X¹ and X² representsa hydrogen atom and in which the other one thereof represents a methylgroup are also preferred. Among these compounds, the rate ofpolymerization is the highest in diacrylate derivatives and the lowestin dimethacrylate derivatives, and the rate of polymerization ofunsymmetrical compounds is intermediate therebetween. Hence, anappropriate compound can be employed on the basis of the intendedapplication. In PSA display devices, dimethacrylate derivatives areespecially preferred.

Sp¹ and Sp² each independently represent a single bond, an alkylenegroup having 1 to 8 carbon atoms, or —O—(CH₂)_(s)—; in an application toPSA display devices, at least one of Sp¹ and Sp² is preferably a singlebond, and compounds in which Sp¹ and Sp² each represent a single bondand compounds in which one of Sp¹ and Sp² is a single bond and in whichthe other one thereof represents an alkylene group having 1 to 8 carbonatoms or —O—(CH₂)_(s)— are preferred. In this case, an alkyl grouphaving a carbon atom number of 1 to 4 is preferably employed, and spreferably ranges from 1 to 4.

Z¹ is preferably —OCH₂—, —CH₂O—, —COO—, —OCO—, —CF₂O—, —OCF₂—, —CH₂CH₂—,—CF₂CF₂—, or a single bond; more preferably —COO—, —OCO—, or a singlebond; and especially preferably a single bond.

C represents a 1,4-phenylene group of which any hydrogen atom isoptionally substituted with a fluorine atom, a trans-1,4-cyclohexylenegroup, or a single bond; and a 1,4-phenylene group and a single bond arepreferred. In the case where C does not represent a single bond butrepresents a ring structure, Z¹ preferably represents a linking group aswell as a single bond; in the case where C represents a single bond, Z¹is preferably a single bond.

From these viewpoints, a preferred ring structure between Sp¹ and Sp² inGeneral Formula (V) is particularly as follows.

In General Formula (V), in the case where C represents a single bond andwhere the ring structure consists of two rings, the ring structure ispreferably represented by any of Formulae (Va-1) to (Va-5), morepreferably Formulae (Va-1) to (Va-3), and especially preferably Formula(Va-1).

(in the formulae, the two ends of each structure are bonded to Sp¹ andSp², respectively)

Polymerizable compounds having such skeletons enable uneven display tobe reduced or eliminated in PSA liquid crystal display devices becausesuch polymerizable compounds have optimum alignment regulating forceafter being polymerized and thus produce a good alignment state.

Accordingly, the polymerizable monomer is especially preferably any ofcompounds represented by General Formulae (V-1) to (V-4), and mostpreferably the compound represented by General Formula (V-2).

(in the formulae, Sp² represents an alkylene group having 2 to 5 carbonatoms)

In the case where the polymerizable monomer is added, polymerization iscarried out even without a polymerization initiator; however, apolymerization initiator may be used to promote the polymerization.Examples of the polymerization initiator include benzoin ethers,benzophenones, acetophenones, benzyl ketals, and acyl phosphine oxides.In order to enhance storage stability, a stabilizer may be added.Examples of usable stabilizers include hydroquinones, hydroquinonemonoalkylethers, tertiary butylcatechol, pyrogallols, thiophenols, nitrocompounds, β-naphthylamines, β-naphthols, and nitroso compounds.

The polymerizable-monomer-containing liquid crystal layer is useful inliquid crystal display devices, and especially useful in liquid crystaldisplay devices driven by an active matrix; hence, such a liquid crystallayer can be used in liquid crystal display devices of a PSA mode, PSVAmode, VA mode, IPS mode, and ECB mode.

The polymerizable monomer contained in thepolymerizable-monomer-containing liquid crystal layer is polymerized bybeing irradiated with ultraviolet with the result that liquid crystalmolecules can be aligned, and such a liquid crystal layer is used inliquid crystal display devices in which the birefringence of the liquidcrystal composition is utilized to control the amount of light that isto be transmitted. Such a liquid crystal layer is useful in liquidcrystal display devices, such as an AM-LCD (active matrix liquid crystaldisplay device), a TN (twisted nematic liquid crystal display device),an STN-LCD (super twisted nematic liquid crystal display device), anOCB-LCD, and an IPS-LCD (in-plane switching liquid crystal displaydevice), particularly useful in an AM-LCD, and can be used intransmissive or reflective liquid crystal display devices.

(Curable Resin Composition)

The sealant used in the liquid crystal display device of the presentinvention is the cured product of a curable resin composition containinga compound having at least one (meth)acrylic group and at least oneepoxy group per molecule.

Any compound having at least one (meth)acrylic group and at least oneepoxy group per molecule can be used; examples thereof include(meth)acrylic acid-modified epoxy resins and urethane-modified(meth)acrylic epoxy resins.

1) (Meth)Acrylic Acid-Modified Epoxy Resin

Any (meth)acrylic acid-modified epoxy resin can be used; for example, itcan be produced by the reaction of (meth)acrylic acid with an epoxyresin in the presence of a basic catalyst in accordance with routineprocedures.

The (meth)acrylic acid-modified epoxy resin is, for example, a partially(meth)acrylated novolac epoxy resin or bisphenol epoxy resin; forinstance, suitable epoxy resins are biphenyl epoxy resins, naphthaleneepoxy resins, tris(hydroxyphenyl)alkyl epoxy resins, andtetrakis(hydroxyphenyl)alkyl epoxy resins. Any epoxy compound can beused as a material for synthesis of the (meth)acrylic acid-modifiedepoxy resin. Examples thereof include bisphenol A epoxy resins,bisphenol E epoxy resins, bisphenol F epoxy resins, bisphenol S epoxyresins, 2,2′-diallyl bisphenol A epoxy resins, hydrogenated bisphenolepoxy resins, polyoxypropylene bisphenol A epoxy resins,propylene-oxide-added bisphenol A epoxy resins, resorcinol epoxy resins,biphenyl epoxy resins, sulfide epoxy resins, diphenyl ether epoxyresins, dicyclopentadiene epoxy resins, naphthalene epoxy resins, phenolnovolac epoxy resins, cresol novolac epoxy resins, trisphenol novolacepoxy resins, dicyclopentadiene novolac epoxy resins, biphenyl novolacepoxy resins, naphthalene phenol novolac epoxy resins, glycidylamineepoxy resins, alkyl polyol epoxy resins, rubber-modified epoxy resins,glycidyl ester compounds, bisphenol A episulphide resins, and alicyclicepoxy resins. Among these, bisphenol A epoxy resins, bisphenol E epoxyresins, bisphenol F epoxy resins, resorcinol epoxy resins, phenolnovolac epoxy resins, and diphenyl ether epoxy resins are preferred.

Examples of commercially available products of the epoxy compounds usedas a material for synthesis of epoxy (meth)acrylate include bisphenol Aepoxy resins such as jER828EL and jER1004 (each manufactured byMitsubishi Chemical Corporation) and EPICLON 850-S (manufactured by DICCorporation); bisphenol F epoxy resins such as jER806 and jER4004 (eachmanufactured by Mitsubishi Chemical Corporation); bisphenol E epoxyresins such as R-710; bisphenol S epoxy resins such as EPICLON EXA1514(manufactured by DIC Corporation); 2,2′-diallyl bisphenol A epoxy resinssuch as RE-810NM (manufactured by Nippon Kayaku Co., Ltd.); hydrogenatedbisphenol epoxy resins such as EPICLON EXA7015 (manufactured by DICCorporation); propylene-oxide-added bisphenol A epoxy resins such asEP-4000S (manufactured by ADEKA CORPORATION); resorcinol epoxy resinssuch as EX-201 (manufactured by Nagase ChemteX Corporation); biphenylepoxy resins such as jERYX-4000H (manufactured by Mitsubishi ChemicalCorporation); sulfide epoxy resins such as YSLV-50TE (manufactured byNippon Steel Chemical Co., Ltd.); biphenyl ether epoxy resins such asYSLV-80DE (manufactured by Nippon Steel Chemical Co., Ltd.);dicyclopentadiene epoxy resins such as EP-40885 (manufactured by ADEKACORPORATION); naphthalene epoxy resins such as EPICLON HP4032 andEPICLON EXA-4700 (each manufactured by DIC Corporation); phenol novolacepoxy resin such as EPICLON N-740, EPICLON N-770, and EPICLON N-775(each manufactured by DIC Corporation) and jER152 and jER154 (eachmanufactured by Mitsubishi Chemical Corporation); o-cresol novolac epoxyresins such as EPICLON N-670-EXP-S (manufactured by DIC Corporation);cresol novolac epoxy resins such as EPICLON N660, EPICLON N665, EPICLONN670, EPICLON N673, EPICLON N680, EPICLON N695, EPICLON N665EXP, andEPICLON N672EXP (each manufactured by DIC Corporation);dicyclopentadiene novolac epoxy resins such as EPICLON HP7200(manufactured by DIC Corporation); biphenyl novolac epoxy resins such asNC-3000P (manufactured by Nippon Kayaku Co., Ltd.); naphthalene phenolnovolac epoxy resins such as ESN-1655 (manufactured by Nippon SteelChemical Co., Ltd.); glycidylamine epoxy resins such as jER630(manufactured by Mitsubishi Chemical Corporation), EPICLON 430(manufactured by DIC Corporation), and TETRAD-X (manufactured byMITSUBISHI GAS CHEMICAL COMPANY, INC.); alkyl polyol epoxy resins suchas ZX-1542 (manufactured by Nippon Steel Chemical Co., Ltd.), EPICLON726 (manufactured by DIC Corporation), EPOLIGHT 80MFA (manufactured bykyoeisha Chemical Co., Ltd.), and DENACOL EX-611 (manufactured by NagaseChemteX Corporation); rubber-modified epoxy resins such as YR-450 andYR-207 (each manufactured by Nippon Steel Chemical Co., Ltd.) andEpolead PB (manufactured by Daicel Corporation); glycidyl estercompounds such as DENACOL EX-147 (manufactured by Nagase ChemteXCorporation); bisphenol A episulphide resins such as jERYL-7000(manufactured by Mitsubishi Chemical Corporation); and YDC-1312,YSLV-80XY, and YSLV-90CR (each manufactured by Nippon Steel ChemicalCo., Ltd.), XAC4151 (manufactured by Asahi Kasei Corp.), jER1031 andjER1032 (each manufactured by Mitsubishi Chemical Corporation), EXA-7120(manufactured by DIC Corporation), and TEPIC (manufactured by NissanChemical Industries, Ltd.). Any alicyclic epoxy resin can be used;examples of commercially available products thereof include Celloxide2021, Celloxide 2080, Celloxide 3000, Celloxide GT300, and EHPE (eachmanufactured by Daicel Corporation).

In particular, for instance, a resorcinol epoxy acrylate which is theepoxy (meth)acrylate can be produced by the reaction of 360 parts byweight of a resorcinol epoxy resin (“EX-201” manufactured by NagaseChemteX Corporation), 2 parts by weight of p-methoxyphenol as apolymerization inhibitor, 2 parts by weight of triethylamine as areaction catalyst, and 210 parts by weight of acrylic acid under refluxwith stirring at 90° C. for 5 hours while air is supplied. Examples ofcommercially available products of the epoxy (meth)acrylate includeEBECRYL 860, EBECRYL 1561, EBECRYL 3700, EBECRYL 3600, EBECRYL 3701,EBECRYL 3703, EBECRYL 3200, EBECRYL 3201, EBECRYL 3702, EBECRYL 3412,EBECRYL 860, EBECRYL RDX63182, EBECRYL 6040, and EBECRYL 3800 (eachmanufactured by DAICEL-CYTEC Company, Ltd.); EA-1020, EA-1010, EA-5520,EA-5323, EA-CHD, and EMA-1020 (each manufactured by Shin NakamuraChemical Co., Ltd.); Epoxy ester M-600A, Epoxy ester 40EM, Epoxy ester70PA, Epoxy ester 200PA, Epoxy ester 80MFA, Epoxy ester 3002M, Epoxyester 3002A, Epoxy ester 1600A, Epoxy ester 3000M, Epoxy ester 3000A,Epoxy ester 200EA, and Epoxy ester 400EA (each manufactured by kyoeishaChemical Co., Ltd.); and Denacol Acrylate DA-141, Denacol AcrylateDA-314, and Denacol Acrylate DA-911 (each manufactured by Nagase ChemteXCorporation).

2) Urethane-Modified (Meth)Acrylic Epoxy Resin

The urethane-modified (meth)acrylic epoxy resin can be, for example,produced by the following technique: a technique in which polyol isallowed to react with di- or higher functional isocyanate and theresulting product is allowed to react with a (meth)acrylic monomerhaving a hydroxyl group and with glycidol, a technique in which di- orhigher functional isocyanate is allowed to react with a (meth)acrylicmonomer having a hydroxyl group and with glycidol without use of polyol,or a technique in which (meth)acrylate having an isocyanate group isallowed to react with glycidol. In particular, for example, 1 mol oftrimethylolpropane is allowed to react with 3 mol of isophoronediisocyanate in the presence of a tin catalyst; and an isocyanate groupremaining in the resulting compound is allowed to react with ahydroxyethyl acrylate which is an acrylic monomer having a hydroxylgroup and with glycidol which is an epoxy having a hydroxyl group,thereby being able to produce the urethane-modified (meth)acrylic epoxyresin.

The polyol is not particularly limited; examples thereof includeethylene glycol, glycerine, sorbitol, trimethylolpropane, and(poly)propylene glycol.

Any isocyanate can be used provided that it is di- or higher functional;examples thereof include isophorone diisocyanate, 2,4-tolylenediisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate,trimethylhexamethylene diisocyanate, diphenylmethane-4,4′-diisocyanate(MDI), hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate,norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate(XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethanetriisocyanate, tris(isocyanatophenyl) thiophosphate, tetramethylxylenediisocyanate, and 1,6,10-undecane triisocyanate.

The (meth)acrylic monomer having a hydroxyl group is not particularlylimited. Examples of a monomer of which the molecules each have onehydroxyl group include hydroxyethyl (meth) acrylate, hydroxypropyl(meth)acrylate, and hydroxybutyl (meth)acrylate; and examples of amonomer of which the molecules each have two or more hydroxyl groupsinclude epoxy (meth)acrylates such as bisphenol A-modified epoxy(meth)acrylate. These may be used alone or in combination.

In the curable resin composition, the ratio of a (meth)acrylic group toan epoxy group (acryl:epoxy) is preferably from 40:60 to 95:5. In thecase where the equivalent ratio of a (meth)acrylic group is less than40, photoreactivity is decreased with the result that irradiating thesealant with light after adjustment of a gap cannot give initialtemporary curing and that components of the sealant also greatly flowinto liquid crystal in some cases; in the case where the equivalentratio exceeds 95, adhesiveness and moisture permeability may becomeinsufficient. The equivalent ratio is more preferably from 50:50 to80:20.

The compound having at least one (meth)acrylic group and at least oneepoxy group per molecule preferably has a hydrogen-bonding group inorder to reduce compatibility with liquid crystal for elimination ofcontamination and to prevent problematic defective display such asvoids, uneven alignment, and screen burn-in; for example, it ispreferred that the compound have a hydroxyl group and/or a urethanebond.

The compound having at least one (meth)acrylic group and at least oneepoxy group per molecule preferably has at least one molecular skeletonselected from a biphenyl skeleton, a naphthalene skeleton, a bisphenolskeleton, and a partially (meth)acrylated novolac epoxy resin. It canenhance thermal resistance of the curable resin composition in thepresent invention.The compound having at least one (meth)acrylic group and at least oneepoxy group per molecule preferably has a number average molecularweight of 300 or more. A number average molecular weight of less than300 causes components of the sealant to flow into liquid crystal andresults in easily disrupting molecular alignment in some cases. Thenumber average molecular weight is preferably 3000 or less. A numberaverage molecular weight of greater than 3000 may cause viscositycontrol to be difficult in some cases. In use of the compound having atleast one (meth)acrylic group and at least one epoxy group per moleculeas a curable resin, a curable resin composition of the present inventionis cured and then subjected to infrared spectroscopy, and the infraredspectroscopy shows an absorption peak of a carbonyl group derived from a(meth)acrylic group. If an epoxy group and a hydroxyl group derived fromthe epoxy group are present, the absorption peaks thereof can be alsoobserved.

The curable resin composition containing the compound having at leastone (meth)acrylic group and at least one epoxy group per moleculepreferably has a hydrogen-bonding functional group value from 3×10⁻³ to5×10⁻³ mol/g. In such a curable resin composition, hydrogen bonds areformed in molecules; hence, in the case where the curable resincomposition is used as a sealant, the composition is less likely to flowinto liquid crystal before and after curing thereof and therefore hardlycontaminates liquid crystal, which leads to a reduction in problematicdefective display such as voids, uneven alignment, and screen burn-in.Thus, such a curable resin composition is preferred.

The hydrogen bonds are formed by compounds having functional groups orresidues having hydrogen-bonding properties, e.g., compounds havingfunctional groups such as a —OH group, a —NH2 group, a —NHR group (Rrepresents aromatics, aliphatic hydrocarbons, or derivatives thereof), a—COOH group, a —CONH2 group, and a —NHOH group or compounds havingresidues in their molecules, such as a —NHCO— bond, a —NH— bond, a—CONHCO— bond, and a —NH—NH— bond. The above-mentioned hydrogen-bondingfunctional group value is a value which can be obtained from Equation 1in the case where one type of the compounds having hydrogen-bondingfunctional groups is used.Hydrogen-bonding Functional Group Value (HX)(mol/g)=(Number ofHydrogen-bonding Functional Groups in Compound X perMolecule)/(Molecular Weight of Compound X)  (Equation 1)

In the case where the compound having a hydrogen-bonding functionalgroup is a mixture of multiple resins, the hydrogen-bonding functionalgroup value can be obtained by distribution based on the amount of eachcompound having a hydrogen-bonding functional group per unit weight(weight fraction). For example, if the compound having ahydrogen-bonding functional group consists of a compound A, a compoundB, and a compound C, the hydrogen-bonding functional group value isrepresented by Equation 2.Hydrogen-bonding Functional Group Value(HABC)=H_(A)P_(A)+H_(B)P_(B)+H_(C)P_(C)  (Equation 2)(Pα represents the weight fraction of a compound α)A hydrogen-bonding functional group value of less than 3×10⁻³ mol/gcauses components of the curable resin composition to flow into liquidcrystal and results in easily disrupting alignment of liquid crystalmolecules, and a hydrogen-bonding functional group value of greater than5×10⁻³ mol/g enhances the moisture permeability of the cured product andresults in easy intrusion of moisture into a liquid crystal displaydevice.

A single compound having a hydrogen-bonding functional group may be usedso that the hydrogen-bonding functional group value is within theabove-mentioned range, or two or more compounds having hydrogen-bondingfunctional groups may be used in combination so that thehydrogen-bonding functional group value is adjusted to be within theabove-mentioned range. In other words, the average of thehydrogen-bonding functional group values of compounds havinghydrogen-bonding functional groups, which are to be used, may be withinthe above-mentioned range.

The curable resin composition containing the compound having at leastone (meth)acrylic group and at least one epoxy group per moleculepreferably has a volume resistivity of not less than 1×10¹³ Ω·cm aftercuring. A volume resistivity of less than 1×10¹³ Ω·cm shows that asealant contains an ionic impurity, and use of such a sealant causesionic impurities to flow into liquid crystal during application ofelectricity, which results in a decrease in the voltage holding ratio(VHR) of the liquid crystal layer, an increase in ion density, and theoccurrence of defective displays such as voids, uneven alignment, andscreen burn-in.

The curable resin composition containing the compound having at leastone (meth)acrylic group and at least one epoxy group per moleculepreferably has a specific resistance from 1.0×10⁶ to 1.0×10¹⁰ Ω·cmbefore curing. At a specific resistance of less than 1.0×10⁶ Ω·cm, asealant containing such a curable resin composition flows into liquidcrystal, which causes a decrease in the voltage holding ratio (VHR) ofthe liquid crystal layer, an increase in ion density, and defectivedisplays such as voids, uneven alignment, and screen burn-in. A specificresistance of greater than 1.0×10¹⁰ Ω·cm may impair adhesion to asubstrate.

The curable resin composition containing the compound having at leastone (meth)acrylic group and at least one epoxy group per molecule maycontain a resin having (meth)acryloyloxy group and/or a resin having anepoxy group; in particular, resins explained in “Resin Having(Meth)acryloyloxy Group” and “Resin Having Epoxy Group” which will bedescribed later can be used. In any case of using such resins, thepreferred upper limit of the ratio of the epoxy group to the total ofthe (meth)acrylic group and the epoxy resin is 40 mol %. At a ratioexceeding 40 mol %, the solubility of the composition in liquid crystalbecomes excessive and may impair display characteristics.

(Resin Having (Meth)Acryloyloxy Group)

The resin having a (meth)acryloyloxy group refers to the followingresins: for example, ester compounds produced by the reaction of acompound having a hydroxyl group with a (meth)acrylic acid and urethane(meth)acrylates produced by the reaction of a (meth)acrylic acidderivative having a hydroxyl group with isocyanate.

(1) Ester Compounds Produced by Reaction of Compound Having HydroxylGroup with (Meth)Acrylic Acid

Any ester compound produced by the reaction of a compound having ahydroxyl group with a (meth)acrylic acid can be used. Examples ofmonofunctional ester compounds include 2-hydroxyethyl (meth)acrylate,2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate,2-hydroxybutyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl(meth)acrylate, isooctyl (meth)acrylate, lauryl (meth)acrylate, stearyl(meth)acrylate, isobornyl (meth)acrylate, cyclohexyl (meth)acrylate,2-methoxyethyl (meth)acrylate, methoxyethylene glycol (meth)acrylate,2-ethoxyethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, benzyl(meth)acrylate, ethylcarbitol (meth)acrylate, phenoxyethyl(meth)acrylate, phenoxydiethylene glycol (meth)acrylate,phenoxypolyethylene glycol (meth)acrylate, methoxypolyethylene glycol(meth)acrylate, 2,2,2-trifluoroethyl (meth)acrylate,2,2,3,3-tetrafluoropropyl (meth)acrylate, 1H,1H,5H-octafluoropentyl(meth)acrylate, imide (meth)acrylate, methyl (meth)acrylate, ethyl(meth)acrylate, n-butyl (meth)acrylate, propyl (meth)acrylate, n-butyl(meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate,n-octyl (meth)acrylate, isononyl (meth)acrylate, isomyristyl(meth)acrylate, 2-butoxyethyl (meth)acrylate, 2-phenoxyethyl(meth)acrylate, bicyclopentenyl (meth)acrylate, isodecyl (meth)acrylate,diethylaminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate,2-(meth)acryloyloxyethyl succinic acid, 2-(meth)acryloyloxyethylhexahydrophthalic acid, 2-(meth)acryloyloxyethyl 2-hydroxypropylphthalate, glycidyl (meth)acrylate, and 2-(meth)acryloyloxyethylphosphate.

Among the ester compounds produced by the reaction of a compound havinga hydroxyl group with a (meth)acrylic acid, any difunctional estercompound can be used; examples thereof include 1,4-butanedioldi(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,6-hexanedioldi(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanedioldi(meth)acrylate, 2-n-butyl-2-ethyl-1,3-propanediol di(meth)acrylate,dipropylene glycol di(meth)acrylate, tripropylene glycoldi(meth)acrylate, polypropylene glycol di(meth)acrylate, ethylene glycoldi(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethyleneglycol di(meth)acrylate, polyethylene glycol di(meth)acrylate,propylene-oxide-added bisphenol A di(meth)acrylate, ethylene-oxide-addedbisphenol A di(meth)acrylate, ethylene-oxide-added bisphenol Fdi(meth)acrylate, dimethylol dicyclopentadiene di(meth)acrylate,1,3-butylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate,ethylene-oxide-modified isocyanuric acid di(meth)acrylate,2-hydroxy-3-acryloyloxypropyl di(meth)acrylate, carbonate dioldi(meth)acrylate, polyetherdiol di(meth)acrylate, polyesterdioldi(meth)acrylate, polycaprolactonediol di(meth)acrylate, andpolybutadienediol di(meth)acrylate.

Among the ester compounds produced by the reaction of a compound havinga hydroxyl group with a (meth)acrylic acid, any tri- or higherfunctional ester compound can be used; examples thereof includepentaerythritol tri(meth)acrylate, trimethylolpropane tri(meth)acrylate,propylene-oxide-added trimethylolpropane tri(meth)acrylate,ethylene-oxide-added trimethylolpropane tri(meth)acrylate,caprolactone-modified trimethylolpropane tri(meth)acrylate,ethylene-oxide-added isocyanuric acid tri(meth)acrylate,dipentaerythritol penta(meth)acrylate, dipentaerythritolhexa(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate,pentaerythritol tetra(meth)acrylate, glycerine tri(meth)acrylate,propylene-oxide-added glycerine tri(meth)acrylate, andtris(meth)acryloyloxyethyl phosphate.

2) Urethane(Meth)Acrylate Produced by Reaction of Acrylic AcidDerivative Having Hydroxyl Group with Isocyanate

Any urethane(meth)acrylate produced by the reaction of a (meth)acrylicacid derivative having a hydroxyl group with isocyanate can be used; forinstance, a urethane (meth)acrylate can be produced by the reaction oftwo equivalents of a (meth)acrylic acid derivative having a hydroxylgroup with one equivalent of a compound having two isocyanate groups inthe presence of a tin compound as a catalyst.Any isocyanate can be used as a material of the urethane(meth)acrylateproduced by the reaction of a (meth)acrylic acid derivative having ahydroxyl group with isocyanate; examples thereof include isophoronediisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate,hexamethylene diisocyanate, trimethylhexamethylene diisocyanate,diphenylmethane-4,4′-diisocyanate (MDI), hydrogenated MDI, polymericMDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidinediisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysinediisocyanate, triphenylmethane triisocyanate, tris(isocyanatophenyl)thiophosphate, tetramethylxylene diisocyanate, and 1,6,10-undecanetriisocyanate.

The isocyanate to be used as a material of the urethane (meth)acrylateproduced by the reaction of a (meth)acrylic acid derivative having ahydroxyl group with isocyanate can be also, for instance, achain-extended isocyanate compound which is obtainable by the reactionof an excess amount of an isocyanate with a polyol such as ethyleneglycol, glycerine, sorbitol, trimethylolpropane, (poly)propylene glycol,carbonate diol, polyether diol, polyester diol, or polycaprolactonediol.

Any (meth)acrylic acid derivative having a hydroxyl group can be used;examples thereof include commercially available products such as2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate,4-hydroxybutyl (meth)acrylate, and 2-hydroxybutyl (meth)acrylate;mono(meth)acrylates of dihydric alcohols such as ethylene glycol,propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, andpolyethylene glycol; mono(meth)acrylates or di(meth)acrylates oftrihydric alcohols such as trimethylolethane, trimethylolpropane, andglycerine; and epoxy (meth)acrylates such as bisphenol A-modified epoxy(meth)acrylate.

In particular, for example, the urethane (meth)acrylate can be producedas follows: 0.2 parts by weight of BHT as a polymerization inhibitor,0.01 parts by weight of dibutyl tin dilaurate as a reaction catalyst,and 666 parts by weight of isophorone diisocyanate are added to 134parts by weight of trimethylolpropane; the reaction is carried out for 2hours under reflux with stirring at 60° C.; then 51 parts by weight of2-hydroxyethyl acrylate is added thereto; and the reaction is performedfor 2 hours under reflux with stirring at 90° C. while air is supplied.

Examples of commercially available products of the urethane(meth)acrylate include M-1100, M-1200, M-1210, and M-1600 (eachmanufactured by TOAGOSEI CO., LTD.); Ebecryl 230, Ebecryl 270, Ebecryl4858, Ebecryl 8402, Ebecryl 8804, Ebecryl 8803, Ebecryl 8807, Ebecryl9260, Ebecryl 1290, Ebecryl 5129, Ebecryl 4842, Ebecryl 210, Ebecryl4827, Ebecryl 6700, Ebecryl 220, and Ebecryl 2220 (each manufactured byDAICEL-CYTEC Company, Ltd.); Art Resin UN-9000H, Art Resin UN-9000A, ArtResin UN-7100, Art Resin UN-1255, Art Resin UN-330, Art Resin UN-3320HB,Art Resin UN-1200TPK, and Art Resin SH-500B (each manufactured by Negamichemical industrial co., ltd.); U-122P, U-108A, U-340P, U-4HA, U-6HA,U-324A, U-15HA, UA-5201P, UA-W2A, U-1084A, U-6LPA, U-2HA, U-2PHA,UA-4100, UA-7100, UA-4200, UA-4400, UA-340P, U-3HA, UA-7200, U-2061BA,U-10H, U-122A, U-340A, U-108, U-6H, and UA-4000 (each manufactured byShin Nakamura Chemical Co., Ltd.); and AH-600, AT-600, UA-306H, AI-600,UA-101T, UA-101I, UA-306T, and UA-3061.

The curable resin preferably has at least one hydrogen-bondingfunctional group per molecule in order to further reduce flowing ofcomponents of the sealant, which is used in a liquid-crystal-droppingtechnique according to the present invention, into liquid crystal in itsuncured state. The hydrogen-bonding functional group is not particularlylimited; examples thereof include functional groups, such as a —OHgroup, a —SH group, a —NHR group (R represents an aromatics, aliphatichydrocarbons, or derivatives thereof), a —COOH group, and a —NHOH group,and residues remaining in molecules, such as —NHCO—, —NH—, —CONHCO—, and—NH—NH—. Among these, a —OH group is preferred because it is easy to beintroduced.

Resin Having An Epoxy Group:

The sealant in the present invention may contain a resin having an epoxygroup.

The resin having an epoxy group is not particularly limited; examplesthereof include epichlorohydrin derivatives, alicyclic epoxy resins, andcompounds produced by the reaction of isocyanate with glycidol.

Any resin having an epoxy group can be used, and examples thereofinclude bisphenol A epoxy resins, bisphenol F epoxy resins, bisphenol Sepoxy resins, 2,2′-diallyl bisphenol A epoxy resins, hydrogenatedbisphenol epoxy resins, propylene-oxide-added bisphenol A epoxy resins,resorcinol epoxy resins, biphenyl epoxy resins, sulfide epoxy resins,diphenyl ether epoxy resins, dicyclopentadiene epoxy resins, naphthaleneepoxy resins, phenol novolac epoxy resins, o-cresol novolac epoxyresins, dicyclopentadiene novolac epoxy resins, biphenyl novolac epoxyresins, naphthalene phenol novolac epoxy resins, glycidylamine epoxyresins, alkyl polyol epoxy resins, rubber-modified epoxy resins,glycidyl ester compounds, and bisphenol A episulphide resins.

Examples of the epichlorohydrin derivatives include bisphenol A epoxyresins such as jER828EL and jER1004 (each manufactured by MitsubishiChemical Corporation) and EPICLON 850-S (manufactured by DICCorporation); bisphenol F epoxy resins such as jER806 and jER4004 (eachmanufactured by Mitsubishi Chemical Corporation); bisphenol S epoxyresins such as EPICLON EXA1514 (manufactured by DIC Corporation);2,2′-diallyl bisphenol A epoxy resins such as RE-810NM (manufactured byNippon Kayaku Co., Ltd.); hydrogenated bisphenol epoxy resins such asEPICLON EXA7015 (manufactured by DIC Corporation); propylene-oxide-addedbisphenol A epoxy resins such as EP-40005 (manufactured by ADEKACORPORATION); resorcinol epoxy resins such as EX-201 (manufactured byNagase ChemteX Corporation); biphenyl epoxy resins such as jERYX-4000H(manufactured by Mitsubishi Chemical Corporation); sulfide epoxy resinssuch as YSLV-50TE (manufactured by Nippon Steel Chemical Co., Ltd.);biphenyl ether epoxy resins such as YSLV-80DE (manufactured by NipponSteel Chemical Co., Ltd.); dicyclopentadiene epoxy resins such asEP-4088S (manufactured by ADEKA CORPORATION); naphthalene epoxy resinssuch as EPICLON HP4032 and EPICLON EXA-4700 (each manufactured by DICCorporation); phenol novolac epoxy resin such as EPICLON N-770(manufactured by DIC Corporation); o-cresol novolac epoxy resins such asEPICLON N-670-EXP-S (manufactured by DIC Corporation); dicyclopentadienenovolac epoxy resins such as EPICLON HP7200 (manufactured by DICCorporation); biphenyl novolac epoxy resins such as NC-3000P(manufactured by Nippon Kayaku Co., Ltd.); naphthalene phenol novolacepoxy resins such as ESN-165S (manufactured by Nippon Steel ChemicalCo., Ltd.); glycidylamine epoxy resins such as jER630 (manufactured byMitsubishi Chemical Corporation), EPICLON 430 (manufactured by DICCorporation), TETRAD-X (manufactured by MITSUBISHI GAS CHEMICAL COMPANY,INC.); alkyl polyol epoxy resins such as ZX-1542 (manufactured by NipponSteel Chemical Co., Ltd.), EPICLON 726 (manufactured by DICCorporation), EPOLIGHT 80MFA (manufactured by kyoeisha Chemical Co.,Ltd.), and DENACOL EX-611 (manufactured by Nagase ChemteX Corporation);rubber-modified epoxy resins such as YR-450 and YR-207 (eachmanufactured by Nippon Steel Chemical Co., Ltd.) and Epolead PB(manufactured by Daicel Corporation); glycidyl ester compounds such asDENACOL EX-147 (manufactured by Nagase ChemteX Corporation); bisphenol Aepisulphide resins such as jERYL-7000 (manufactured by MitsubishiChemical Corporation); and YDC-1312, YSLV-80XY, and YSLV-90CR (eachmanufactured by Nippon Steel Chemical Co., Ltd.), XAC4151 (manufacturedby Asahi Kasei Corp.), jER1031 and jER1032 (each manufactured byMitsubishi Chemical Corporation), EXA-7120 (manufactured by DICCorporation), and TEPIC (manufactured by Nissan Chemical Industries,Ltd.).

The above-mentioned alicyclic epoxy resins are not particularly limited;examples of commercially available products thereof include Celloxide2021, Celloxide 2080, Celloxide 3000, Epolead GT300, and EHPE (eachmanufactured by Daicel Corporation).

Any compound produced by the reaction of isocyanate with glycidol can beused; for instance, such a compound can be produced by the reaction of acompound having two isocyanate groups with two equivalents of glycidolin the presence of a tin compound as a catalyst.Any isocyanate can be used; examples thereof include isophoronediisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate,hexamethylene diisocyanate, trimethylhexamethylene diisocyanate,diphenylmethane-4,4′-diisocyanate (MDI), hydrogenated MDI, polymericMDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidinediisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysinediisocyanate, triphenylmethane triisocyanate, tris(isocyanatophenyl)thiophosphate, tetramethylxylene diisocyanate, and 1,6,10-undecanetriisocyanate.

The isocyanate can be, for instance, a chain-extended isocyanatecompound which is obtainable by the reaction of an excess amount of anisocyanate with a polyol such as ethylene glycol, glycerine, sorbitol,trimethylolpropane, (poly)propylene glycol, carbonate diol, polyetherdiol, polyester diol, or polycaprolactone diol.

The resin having an epoxy group may be, for example, a resin having a(meth)acryloyloxy group and an epoxy group per molecule. An example ofsuch a compound is a partially (meth)acrylic-modified epoxy resinproduced by the reaction of some epoxy groups of a compound having twoor more epoxy groups with (meth)acrylic acids.The curable resin may consist of only the resin having a(meth)acryloyloxy group and an epoxy group per molecule.

The partially (meth)acrylic-modified epoxy resin can be, for example,produced by the reaction of (meth)acrylic acid with an epoxy resin inthe presence of a basic catalyst in accordance with routine procedures.In particular, for instance, 190 g of phenol novolac epoxy resin(“N-770” manufactured by DIC Corporation) is dissolved in 500 ml oftoluene, 0.1 g of triphenylphosphine is added to the solution to makethe solution homogeneous, 35 g of acrylic acid is dropped into theresulting solution for 2 hours under reflux with stirring, the refluxwith stirring is further continued for 6 hours, and then toluene isremoved to produce a partially acrylic-modified phenol novolac epoxyresin in which 50 mol % of epoxy groups have reacted with an acrylicacid (50% acrylated in this case).

An example of commercially available products of the partially(meth)acrylic-modified epoxy resin is UVACURE1561 (manufactured byDAICEL-CYTEC Company, Ltd.).

The curable resin composition containing the compound having at leastone (meth)acrylic group and at least one epoxy group per moleculepreferably contains a curing agent. In particular, it is preferred thata photopolymerization initiator be used. Any photopolymerizationinitiator can be employed; a radical photopolymerization initiator ispreferred, and an alkylphenone photopolymerization initiator, an oximeester photopolymerization initiator, and an acylphosphine oxidephotopolymerization initiator are especially preferred.

Examples of the photopolymerization initiator include benzophenone,2,2-diethoxyacetophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one,1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propane-1-one,benzoyl isopropyl ether, benzyl dimethyl ketal, 1-hydroxycyclohexylphenyl ketone, thioxanthone, and 1,2-octanedione1-[4-(phenylthio)-2-(O-benzoyloxime)]. These photopolymerizationinitiators can be used alone or in combination.

A photopolymerization initiator having a reactive double bond and aphotoreaction initiating part may be used. In particular, abenzoin(ether) compound having a reactive double bond and a hydroxylgroup and/or a urethane bond is preferred. The benzoin(ether) compoundrefers to benzoins and benzoin ethers.

Examples of the reactive double bond include residues such as an allylgroup, a vinyl ether group, and a (meth)acrylic group; in application toa photopolymerization initiator used in a sealant, a (meth)acrylicresidue is preferred because it is highly reactive. Such a reactivedouble bond contributes to an enhancement in weather resistance.The benzoin(ether) compound may have any one of a hydroxyl group and aurethane bond or both of them. In the case where the benzoin(ether)compound does not have any of a hydroxyl group and a urethane bond, thebenzoin(ether) compound added to the sealant may flow into liquidcrystal before curing.

In the benzoin(ether) compound, the reactive double bond and a hydroxylgroup and/or a urethane bond may be at any position on thebenzoin(ether) skeleton; a benzoin(ether) compound having a molecularframework represented by General Formula (1-A) is preferred. Use of acompound having such a molecular framework as a photopolymerizationinitiator enables a reduction in a remaining substance, which leads to adecrease in the amount of outgas.

In the formula, R represents a hydrogen atom or an aliphatic hydrocarbonresidue having four or less carbon atoms. In the case where R is analiphatic hydrocarbon residue having carbon atoms of greater than four,use of the photopolymerization initiator contributes to an enhancementin storage stability but may reduce reactivity owing to the sterichindrance of substituents.The amount of the photopolymerization initiator is preferably in therange of 0.1 to 10 parts by weight relative to 100 parts by weight ofthe curable resin. At an amount of less than 0.1 parts by weight, thefunction of initiating photopolymerization is insufficient with theresult that a good effect is not produced in some cases; at an amount ofgreater than 10 parts by weight, many unreacted parts ofphotopolymerization initiator may remain with the result that weatherresistance is impaired in some cases. The amount is more preferably from1 to 5 weight parts.

The curable resin composition containing the compound having at leastone (meth)acrylic group and at least one epoxy group per moleculepreferably contains a thermosetting agent as well. The thermosettingagent promotes the reaction and crosslinking of the epoxy group and/oracrylic group in the curable resin composition by heating and serves toenhance the adhesion and moisture resistance of the curable resincomposition after curing. Any thermosetting agent can be used, and alatent thermosetting agent having a melting point of 100° C. or higheris preferably employed. Use of a thermosetting agent having a meltingpoint of less than 100° C. may significantly degrade storage stability.

Examples of such a thermosetting agent include hydrazide compounds suchas 1,3-bis[hydrazinocarbonoethyl-5-isopropylhydantoin]; dicyandiamide;guanidine derivatives; imidazole derivatives such as1-cyanoethyl-2-phenylimidazole, N-[2-(2-methyl-1-imidazolyl)ethyl]urea,2,4-diamino-6-[2′-methylimidazolyl-(1′)]ethyl-s-triazine,N,N′-bis(2-methyl-1-imidazolylethyl)urea,N,N′-(2-methyl-1-imidazolylethyl)adipoamide,2-phenyl-4-methyl-5-hydroxymethylimidazole, and2-phenyl-4,5-dihydroxymethylimidazole; modified aliphatic polyamines;acid anhydrides such as tetrahydrophthalic anhydride and ethyleneglycol-bis(anhydrotrimellitate); and addition products of various aminesand epoxy resins. These materials may be used alone or in combination.

In the case where an acrylic acid-modified epoxy resin is used as thecompound having at least one (meth)acrylic group and at least one epoxygroup per molecule, the reactivity of the acrylic epoxy resin greatlyvaries on the basis of its structure; in the case where aurethane-modified epoxy resin is used, its stability gives excellentstorage stability even when a highly reactive thermosetting agent isused. In the case where a (meth)acrylic acid-modified epoxy resin isemployed, a thermosetting agent having a melting point of not less than100° C. and small reactivity is preferred in terms of storage stabilitybecause the (meth)acrylic acid-modified epoxy resin is highly reactive.

The amount of the thermosetting agent is preferably in the range of 5 to60 parts by weight, and more preferably 10 to 50 parts by weightrelative to 100 parts by weight of the curable compound. At an amountout of such a range, the adhesiveness and chemical resistance of thecured product may be reduced, which result in promoting degradation ofthe properties of liquid crystal in an operation test under ahigh-temperature and humidity environment in some cases.

The thermosetting agent is preferably a coated thermosetting agent whichwill be described later. Using the coated thermosetting agent in thepresent invention gives a sealant significantly high storage stabilityeven when the sealant is one-package type.

In particular, a coated thermosetting agent in which the surface of asolid thermosetting agent is coated with fine particles that are lessvolatile and less soluble in organic materials is used, thereby beingable to produce a sealant which has a high storage stability even thoughthe curing agent has been preliminarily added to the sealant.The term “solid thermosetting agent” herein refers to a curing agentwhich is in the form of a solid at room temperature and which is meltedor softened by heating to start reacting with a curable resin. Any solidthermosetting agent can be used provided that its melting point orsoftening point is greater than or equal to room temperature; examplesof such a solid thermosetting agent include solid amine compounds,phenolic compounds, and acid anhydrides. Among these, solid aminecompounds are preferred because they are highly reactive at lowtemperature.The term “solid amine compounds” refers to solid compounds each havingone or more primary to tertiary amino groups per molecule. Examplesthereof include aromatic amines such as methaphenylene diamine anddiaminodiphenyl methane; imidazole compounds such as 2-methylimidazole,1,2-dimethylimidazole, and 1-cyanoethyl-2-methylimidazole; imidazolinecompounds such as 2-methylimidazoline; and dihydrazide compounds such assebacic acid dihydrazide and isophthalic acid dihydrazide. Examples ofcommercially available products of the solid amine compounds includeamine adducts, such as Amicure PN-23 and Amicure MY-24 (each manufactureby Ajinomoto Fine-Techno Co., Inc.), and dicyandiamide.

Examples of the polyhydric phenolic compounds include polyphenoliccompounds and novolac phenolic resins. Examples of commerciallyavailable products of the polyhydric phenolic compounds include jERCURE170, jERCURE YL 6065, and jERCURE MP402FPI (each manufactured byMitsubishi Chemical Corporation).

Examples of the acid anhydride include glycerinebis(anhydrotrimellitate), ethylene glycol-bis(anhydrotrimellitate),tetrahydrophthalic anhydride, hexahydrophthalic anhydride,4-methylhexahydrophthalic anhydride, and 3-methyltetrahydrophthalicanhydride. Examples of commercially available products of these acidanhydrides include jERCURE YH 306 and YH 307 (each manufactured byMitsubishi Chemical Corporation).The solid thermosetting agent may have any average particle size; theaverage particle size is preferably in the range of 0.1 to 50 μm. At anaverage particle size of less than 0.1 μm, the surface cannot beefficiently coated with the fine particles in some cases; at an averageparticle size of greater than 50 μm, the curing agent added to thesealant may be precipitated during storage thereof or may cause unevencuring. The average particle size is more preferably from 0.5 to 10 μm.

The fine particles which coat the surfaces of the particles of the solidthermosetting agent can be oxides, hydroxides, and halides of Si, Al,Ti, Fe, Mn, and Mg; styrene beads; or particulate rubber. These types offine particles may be used alone or in combination.

The average particle size of the fine particles is preferably not morethan 0.05 μm. At an average particle size of greater than 0.05 μm, thesurfaces of the particles of the solid thermosetting agent cannot beefficiently coated in some cases. The average particle size is morepreferably not more than 0.03 μm. It is preferred that the particle sizeof the fine particles be not more than 10% of that of the particles ofthe solid thermosetting agent. In the case where it exceeds 10% , thefunction of controlling the reactivity is insufficient in some cases.The weight ratio of the particles of the solid thermosetting agent tothe fine particles in the coated thermosetting agent is preferably from50:1 to 3:1. In the case where the weight ratio of the particles of thesolid thermosetting agent is greater than 50, the function ofcontrolling the reactivity is insufficient in some cases; in the casewhere it is less than 3, fine particles are excessive, which results inimpairing the curing function in some cases. The weight ratio is morepreferably from 20:1 to 5:1.

The surfaces of the particles of the solid thermosetting agent can becoated with the fine particles by any technique; for example, atechnique in which the particles of the solid thermosetting agent aremixed with fine particles with a commercially available blender in acontainer to make the mixture homogeneous can be used. The amount of thecoated thermosetting agent in the curable resin composition ispreferably in the range of 1 to 100 parts by weight relative to 100parts by weight of the curable resin composition. If the amount is lessthan 1 part by weight, the curing may become insufficient; if the amountis greater than 100 parts by weight, an excess amount of thethermosetting agent remains, which results in impairing the physicalproperties of a cured product to be obtained, such as toughness, in somecases.

The coated thermosetting agent added to the curable resin compositionhas a high storage stability in storage at normal temperature becausethe contact of the solid thermosetting agent with the polymerizableresin is reduced as much as possible owing to the fine particles whichare present on the surface thereof; in a curing process, the solidthermosetting agent becomes liquid by application of heat and istherefore brought into contact with the curable resin without beinginhibited by the fine particles, so that the curing reaction immediatelybegins. Accordingly, the storage stability of the curable resincomposition is improved. The coated thermosetting agent can be verysimply produced at a normal temperature in a short time withoutrequiring a specific reaction.

The curable resin composition containing the compound having at leastone (meth)acrylic group and at least one epoxy group per molecule maycontain a radical polymerization inhibitor.

Examples of the radical polymerization inhibitor include 2,6-di-t-butylcresol, butylated hydroxyanisole, 2,6-di-t-butyl-4-ethylphenol, stearylβ-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, 2,2′-methylenebis(4-methyl-6-t-butylphenol), 2,2′-methylenebis(4-ethyl-6-t-butylphenol), 4,4′-thiobis-3-methyl-6-t-butylphenol),4,4-butylidene bis(3-methyl-6-t-butylphenol),3,9-bis[1,1-dimethyl-2-[β-(3-t-butyl-4-hydroxy-5-methylphenyl)propionyloxy]ethyl], 2,4,8,10-tetraoxaspiro[5,5]undecane,tetrakis-[methylene-3-(3′,5′-di-t-butyl-4′-hydroxyphenyl)propionate]methane,1,3,5-tris(3′,5′-di-t-butyl-4′-hydroxybenzyl)-sec-triazine-2,4,6-(1H,3H,5H)trione,hydroquinone, and paramethoxyphenol. These radical polymerizationinhibitors may be used alone or in combination.

The lower limit and upper limit of the amount of the radicalpolymerization inhibitor are 0.1 parts by weight and 0.4 parts by weightrelative to 100 parts by weight of the curable resin composition,respectively. In the case where the amount of the radical polymerizationinhibitor is less than 0.1 parts by weight, the radical polymerizationinhibitor is quickly consumed by the small amount of radicals which aregenerated when slight light is present in production of liquid crystaldisplay devices; hence, the sealant is unintentionally cured when it isexposed to slight light which is not for curing the sealant. In the casewhere the amount of the radical polymerization inhibitor is greater than0.4 parts by weight, a sealant to be produced is significantly lesscurable when it is irradiated with ultraviolet; hence, the sealant isnot cured in some cases even though it is irradiated with ultravioletfor the purpose of being cured.

The curable resin composition containing the compound having at leastone (meth)acrylic group and at least one epoxy group per moleculepreferably further contains a silane coupling agent. The silane couplingagent primarily serves as an adhesion aid for well attaching the sealantand the substrates of the liquid crystal display device to each other.In addition, in the case where inorganic and organic fillers are used toimprove the adhesiveness by the effect of stress dispersion and thecoefficient of linear expansion, the silane coupling agent may be usedin a process in which the surfaces of the fillers are treated with thesilane coupling agent to enhance the interaction of the resin containedin the sealant with the fillers.

The silane coupling agent is preferably a silane compound having atleast one functional group selected from the group (2-A) and at leastone functional group selected from the group (2-B).

Specific examples of such a silane compound includeγ-aminopropyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane,γ-glycidoxypropyltrimethoxysilane, andγ-isocyanatepropyltrimethoxysilane. These silane compounds can be usedalone or in combination.Using the silane compound having such a structure as a silane couplingagent enables an enhancement in adhesiveness to substrates and alsoeliminates flowing of components of the curable resin into liquidcrystal owing to a chemical bond of the silane compound to the curableresin via a functional group selected from the group 2-B.

The silane compound is mixed with components of the curable resin andthen subjected to a thermal treatment. The thermal treatment causes thesilane compound to be chemically bonded to the components of the curingresin via the functional group selected from the group 2-B. The thermaltreatment is preferably performed under stirring of the resin mixture inorder to enhance the reaction efficiency. The stirring is carried out inany way; for example, a general technique, such as rotating a stirrer orstirring blades by means of a motor, can be used. The temperature in thethermal treatment is preferably in the range of 30 to 70° C. At atemperature lower than 30° C., the reaction of the silane compound withthe curing resin is insufficient in some cases; at a temperature higherthan 70° C., curing may begin owing to the heat. The temperature is morepreferably from 40 to 60° C. The duration of the thermal treatment ispreferably from one to two hours. In the case where the duration isshorter than one hour, every functional group of the silane compounddoes not react, and thus unreacted substances may remain in some cases.

The residual rate of at least one functional group selected from thegroup 2-B after the thermal treatment is not more than 10%. At aresidual rate of greater than 10%, the functional group reacts withcomponents of the resin during storage, which results in an increase inthe viscosity and pollution of liquid crystal due to flowing ofcomponents into the liquid crystal. The residual rate of at least onefunctional group selected from the group 2-B can be calculated from therelative ratio between the intensity of the peaks of the functionalgroups in the silane compound and the intensity thereof after thethermal treatment by 1H-NMR analysis.

The curable resin composition containing the compound having at leastone (meth)acrylic group and at least one epoxy group per molecule maycontain a filler as well in order to control viscosity and to improvethe adhesiveness by the effect of stress dispersion.

Any filler can be used; examples of usable fillers include inorganicfillers such as talc, asbestos, silica, diatomaceous earth, smectite,bentonite, calcium carbonate, magnesium carbonate, alumina,montmorillonite, diatomaceous earth, zinc oxide, iron oxide, magnesiumoxide, tin oxide, titanium oxide, magnesium hydroxide, aluminumhydroxide, glass beads, silicon nitride, barium sulfate, gypsum, calciumsilicate, sericite-activated clay, and aluminum nitride and organicfillers such as polyester microparticles, polyurethane microparticles,vinyl polymer microparticles, acrylic polymer microparticles, and rubbermicroparticles.The filler may have any shape; it may have a regular shape such as aspherical shape, an acicular shape, or a planar shape or may beamorphous.

The curable resin composition containing the compound having at leastone (meth)acrylic group and at least one epoxy group per molecule maycontain fine resin particles as well.

The fine resin particles consist of core particles formed of a resinhaving a rubber elasticity and a glass transition temperature of notmore than −10° C. and shell layers formed of a resin having a glasstransition temperature from 50 to 150° C. on the surfaces of the coreparticles.The glass transition temperature is herein measured by a general DSCtechnique at a temperature increase rate of 10° C./min unless otherwisespecified.The resin having a rubber elasticity and a glass transition temperatureof not more than −10° C. is not particularly limited; a polymer of a(meth)acrylic monomer is preferred.

Examples of the (meth)acrylic monomer include ethyl acrylate, propylacrylate, n-butyl acrylate, cyclohexyl acrylate, 2-ethylhexyl acrylate,ethyl methacrylate, and butyl methacrylate. These (meth)acrylic monomerscan be used alone for polymerization or in combination forcopolymerization.

The resin having a glass transition temperature from 50 to 150° C. isnot particularly limited. Examples thereof include polymers producedthrough polymerization of isopropyl methacrylate, t-butyl methacrylate,cyclohexyl methacrylate, phenyl methacrylate, methyl methacrylate,styrene, 4-chlorostyrene, 2-ethylstyrene, acrylonitrile, or vinylchloride. These monomers may be used alone or in combination.

The particle size of the fine resin particles is appropriatelydetermined on the basis of the intended purpose; the preferred lowerlimit and upper limit thereof are 0.01 μm and 5 μm, respectively. Withinthis range, the fine resin particles have an enough surface arearelative to the photocurable resin, which effectively gives the swellingeffect of the core layer; in addition, such a particle size can giveworkability for forming a gap between substrates when the fine resinparticles are used in a sealant for liquid crystal display devices.

A technique for producing fine resin particles is not particularlylimited; for example, only the monomer that serves as the core is usedto form core particles through emulsion polymerization, and then anothermonomer that serves as a shell is added thereto and polymerized in orderto form a shell layer on the surface of each core particle. Thepreferred lower limit and upper limit of the amount of the fine resinparticles in the curable resin composition are 15 parts by weight and 50parts by weight relative to 100 parts by weight of the photocurableresin, respectively. At an amount of less than 15 parts by weight, anenhancement in adhesiveness may be insufficient; at an amount of greaterthan 50 parts by weight, the viscosity may be unnecessarily increased.The more preferred upper limit is 20 parts by weight.

(Alignment Film)

In the liquid crystal display device of the present invention, in thecase where alignment films need to be provided on the liquid crystalcomposition sides of the first and second substrates to align themolecules of the liquid crystal composition, the alignment films aredisposed between a color filter of one of the alignment films and theliquid crystal layer in the liquid crystal display device. Eachalignment film, however, has a thickness of not more than 100 nm evenwhen the thickness is large; hence, the alignment films do notcompletely block the interaction between a colorant used in the colorfilter, such as a pigment, and a liquid crystal compound used in theliquid crystal layer.

In a liquid crystal display device in which an alignment film is notused, the interaction between a colorant used in the color filter, suchas a pigment, and a liquid crystal compound used in the liquid crystallayer is larger.

The material of the alignment films can be a transparent organicmaterial such as polyimide, polyamide, BCB (benzocyclobutene polymer),or polyvinyl alcohol; in particular, polyimide alignment films formedthough imidizing of a polyamic acid synthesized from diamine such as analiphatic or alicyclic diamine (e.g., p-phenylenediamine and4,4′-diaminodiphenyl methane), an aliphatic or alicyclic tetracarboxylicacid anhydride such as butanetetracarboxylic acid anhydride or2,3,5-tricarboxycyclopentyl acetic acid anhydride, and an aromatictetracarboxylic acid anhydride such as pyromellitic acid dianhydride arepreferred. In this case, rubbing is generally carried out to give analignment function; however, in the case where each alignment film isused as, for instance, a vertical alignment film, the alignment film canbe used without the alignment function being developed.

Materials usable for the alignment films may be materials in whichcompounds contain, for instance, chalcone, cinnamate, cinnamoyl, or anazo group. Such materials may be used in combination with anothermaterial such as polyimide or polyamide; in this case, the alignmentfilms may be rubbed or treated by a photo-alignment technique.

In general formation of alignment films, the above-mentioned material ofthe alignment films is applied onto substrates by, for example, spincoating to form resin films; besides, uniaxial stretching or aLangmuir-Blodgett technique can be employed.

(Transparent Electrode)

In the liquid crystal display device of the present invention, thematerial of a transparent electrode can be a conductive metal oxide.Usable metal oxides are indium oxide (In₂O₂), tin oxide (SnO₂), zincoxide (ZnO), indium tin oxide (In₂O₂—SnO₂), indium zinc oxide(In₂O₂—ZnO), niobium-doped titanium dioxide (Ti_(1-x)Nb_(x)O₂),fluorine-doped tin oxide, graphene nanoribbon, and metal nanowires;among these, zinc oxide (ZnO), indium tin oxide (In₂O₂—SnO₂), and indiumzinc oxide (In₂O₂—ZnO) are preferred. A transparent conductive filmformed of any of such materials can be patterned by photo-etching or atechnique involving use of a mask.

The liquid crystal display device of the present invention isparticularly useful for active-matrix liquid crystal display devices andcan be applied to liquid crystal display devices of a VA mode, PSVAmode, PSA mode, IPS mode, and ECB mode.

The liquid crystal display devices are combined with a backlight forvarious applications such as liquid crystal television sets, monitors ofcomputers, mobile phones, displays of smartphones, laptops, portableinformation terminals, and digital signage. Examples of the back lightinclude cold-cathode tube backlights and virtually white backlights withtwo peak wavelengths or backlights with three peak wavelengths; in thebacklight with two or three peak wavelengths, light-emitting diodesusing inorganic materials or organic EL devices are used.

EXAMPLES

Although the present invention will now be described further in detailwith reference to Examples, the present invention is not limited toExamples. In compositions which will be described in Examples andComparative Examples, the term “%” refers to “mass %”.

In Examples, the following properties were measured.

T_(ni): Nematic phase-isotropic liquid phase transition temperature (°C.)

Δn: Refractive index anisotropy at 25° C.

Δ∈: Dielectric anisotropy at 25° C.

η: Viscosity at 20° C. (mPa·s)

γ1: Rotational viscosity at 25° C. (mPa·s)

VHR: Voltage holding ratio (%) at 70° C.

(ratio, represented by %, of a measured voltage to the initially appliedvoltage, which was obtained as follows: a liquid crystal composition wasput into a cell having a thickness of 3.5 μm, and the measurement wascarried out under the conditions of an applied voltage of 5 V, a frametime of 200 ms, and a pulse width of 64 μs)

ID: Ion density at 70° C. (pC/cm²)

(ion density obtained as follows: a liquid crystal composition was putinto a cell having a thickness of 3.5 μm, and measurement was carriedout with an MTR-1 (manufactured by TOYO Corporation) under theconditions of an applied voltage of 20 V and a frequency of 0.05 Hz)

Uneven Alignment:

The degree of uneven alignment caused at the position at which a sealantwas in contact with liquid crystal was visually observed in states inwhich electricity was applied and in which electricity was not applied,and the result of the observation was evaluated on the basis of thefollowing four criteria.

-   -   Excellent: No uneven alignment observed    -   Good: Slight uneven alignment observed, but acceptable    -   Bad: Uneven alignment observed, unacceptable    -   Poor: Uneven alignment observed, quite inadequate

Screen Burn-in:

In evaluation of screen burn-in in a liquid crystal display device, acertain fixed pattern was displayed in a display area for 1000 hours,and then an image was shown evenly on the whole of the screen. Then, thedegree of an afterimage of the fixed pattern was visually observed, andresult of the observation was evaluated on the basis of the followingfour criteria:

-   -   Excellent: No afterimage observed    -   Good: Slight afterimage observed, but acceptable    -   Bad: Afterimage observed, unacceptable    -   Poor: Afterimage observed, quite inadequate

Volume Resistivity of Sealant after Curing:

A sealant was evenly applied onto the chromium-deposited surface of achromium-deposited glass substrate in the form of a thin film and thencured by being exposed to ultraviolet into an ultraviolet-cured producthaving a size of 85 mm×85 mm and a thickness of 3 m. Anotherchromium-deposited glass substrate was disposed on the ultraviolet-curedproduct such that its chromium-deposited surface faced theultraviolet-cured product, and this product was compressed for an hourby applying a load thereto under being heated on a hot plate at 120° C.,thereby producing a test sample. The area (S (cm²)) of the sealant inthe test sample was measured; in addition, a constant voltage (V (V))was applied between the chromium-deposited surfaces of the facingchromium-deposited glass substrates with a constant voltage generator(PA36-2A regulated DC power supply manufactured by KENWOOD CORPORATION),and an electric current (A (A)) flowing in the film was measured with anammeter (R644C digital multi-meter manufactured by ADVANTESTCORPORATION). Assuming that the thickness of the sealant was (T (cm)),volume resistivity (Ω·cm) was obtained from the following formula:volume resistivity (Ω·cm)=(V·S)/(A·T). In this case, the applied voltagewas a direct current of 500 V, and the duration of the application was 1minute.

Specific Resistance of Sealant Before Curing:

The specific resistance of a sealant before curing was measured understandard temperature and humidity (20° C., 65% RH) with a specificresistance meter (Type SR-6517 manufactured by TOYO Corporation) and anelectrode for liquid (Type LE-21 manufactured by Ando Electric Co.,Ltd.).

In Examples, compounds are abbreviated as follows.

(Side Chain and Linking Group)

-n —C_(n)H_(2n+1) linear alkyl group having n carbon atoms

n- C_(n)H_(2n+1)— linear alkyl group having n carbon atoms

-On —OC_(n)H_(2n+1) linear alkoxyl group having n carbon atoms

nO- C_(n)H_(2n+1)O— linear alkoxyl group having n carbon atoms

-V —CH═CH₂

V- CH₂═CH—

-V1 - CH═CH—CH₃

1V- CH₃—CH═CH—

-2V - CH₂—CH₂—CH═CH₃

V2- CH₃═CH—CH₂—CH₂—

-2V1 - CH₂—CH₂—CH═CH—CH₃

1V2- CH₃—CH═CH—CH₂—CH₂

-1O- —CH₂O—

—O1- —OCH₂—

(Ring Structure)

[Production of Curable Resin Composition]

Synthesis Example A Synthesis of Acrylic Acid-modified Resorcinol EpoxyResin (A)

In a solvent, 106 parts by weight of a resorcinol epoxy resin (EX-201manufactured by Nagase ChemteX Corporation) and 0.1 parts by weight oftriphenylphosphine were evenly dissolved. Then, 32 parts by weight ofacrylic acid was dropped thereto for 2 hours under reflux with stirring,and the reflux with stirring was subsequently further carried out for 8hours. Then, 100 parts by weight of the obtained resin was filteredthrough a column filled with 30 parts by weight of a nature-originatedbound substance of quartz and kaolin (Sillitin V85 manufactured byHOFFMANN MINERAL GmbH) to adsorb ionic impurities in the reactant, andtoluene was removed, thereby producing a 50% acrylic acid-modifiedresorcinol epoxy resin (A).

Synthesis Example B Synthesis of Acrylic Acid-modified Bisphenol A EpoxyResin (B)

In a solvent, 1280 parts by weight of solid bisphenol A diglycidyl ether(EXA850CRP manufactured by DIC Corporation), 2 parts by weight ofp-methoxyphenol as a polymerization inhibitor, and 2 parts by weight oftriethylamine as a reaction catalyst were evenly dissolved. Then, 270parts by weight of acrylic acid was dropped thereto for 2 hours underreflux with stirring, and the reflux with stirring was subsequentlyfurther carried out at 110° C. under supplying of air to promote thereaction for 5 hours. Then, 100 parts by weight of the obtained resinwas filtered through a column filled with 30 parts by weight of anature-originated bound substance of quartz and kaolin (“Sillitin V85”manufactured by HOFFMANN MINERAL GmbH) to adsorb ionic impurities in thereactant, and toluene was removed, thereby producing a 50% acrylicacid-modified bisphenol A epoxy resin (B).

Synthesis Example C Synthesis of Acrylic Acid-modified Diphenyl EtherEpoxy Resin (C)

Under supplying of air, 1000 parts by weight of diphenyl ether epoxyresin (YSLV-80DE manufactured by Nippon Steel Chemical Co., Ltd.), 2parts by weight of p-methoxyphenol as a polymerization inhibitor, 2parts by weight of triethylamine as a reaction catalyst, and 234 partsby weight of acrylic acid were subjected to reflux with stirring at 90°C. to promote a reaction for 6 hours. Then, 100 parts by weight of theobtained resin was filtered through a column filled with 30 parts byweight of a nature-originated bound substance of quartz and kaolin(“Sillitin V85” manufactured by HOFFMANN MINERAL GmbH) to adsorb ionicimpurities in the reactant, and toluene was removed, thereby producing a50% acrylic acid-modified diphenyl ether epoxy resin (C).

Synthesis Example D Synthesis of Methacrylic Acid-modified Bisphenol EEpoxy Resin (D)

In a solvent, 163 parts by weight of bisphenol E epoxy resin R-1710(manufactured by Printec Corporation) was dissolved. Then, 0.5 parts byweight of p-methoxyphenol as a polymerization inhibitor, 0.5 parts byweight of triethylamine as a reaction catalyst, and 40 parts by weightof methacrylic acid were added to the solution, and the resultingsolution was subjected to reflux with stirring at 90° C. for 5 hoursunder supplying of air to promote a reaction. Then, 100 parts by weightof the obtained resin was filtered through a column filled with 30 partsby weight of a nature-originated bound substance of quartz and kaolin(“Sillitin V85” manufactured by HOFFMANN MINERAL GmbH) to adsorb ionicimpurities in the reactant, and toluene was removed, thereby producing a50% methacrylic acid-modified bisphenol E epoxy resin (curable resin D).

Synthesis Example E Synthesis of Acrylic Acid-modified Phenol NovolacEpoxy Resin (E)

Under supplying of air, 1100 parts by weight of liquid phenol novolacepoxy resin (D.E.N. 431 manufactured by The Dow Chemical Company), 2.2parts by weight of p-methoxyphenol as a polymerization inhibitor, 2.2parts by weight of triethylamine as a reaction catalyst, and 220 partsby weight of acrylic acid were subjected to reflux with stirring at 90°C. to promote a reaction for 5 hours. Then, 100 parts by weight of theobtained resin was filtered through a column filled with 30 parts byweight of a nature-originated bound substance of quartz and kaolin(Sillitin V85 manufactured by HOFFMANN MINERAL GmbH) to adsorb ionicimpurities in the reactant, and toluene was removed, thereby producingan acrylic acid-modified phenol novolac epoxy resin (E) (50% partiallyacrylated product).

Synthesis Example F Synthesis of Urethane-modified Acrylic Epoxy Resin(F)

To 1100 parts by weight of trimethylolpropane, 1.6 parts by weight of3,5-dibutyl-4-hydroxytoluene as a polymerization inhibitor, 0.08 partsby weight of dibutyl tin dilaurate as a reaction catalyst, and 5400parts by weight of isophorone diisocyanate were added, and a reactionwas performed for 2 hours under reflux with stirring at 60° C. Then, 210parts by weight of 2-hydroxyethyl acrylate and 910 parts by weight ofglycidol were added thereto, and the reaction was performed for 2 hoursunder reflux with stirring at 90° C. while air was supplied. Then, 100parts by weight of the obtained resin was filtered through a columnfilled with 30 parts by weight of a nature-originated bound substance ofquartz and kaolin (Sillitin V85 manufactured by HOFFMANN MINERAL GmbH)to adsorb ionic impurities in the reactant, and toluene was removed,thereby producing a urethane-modified acrylic epoxy resin (F).

Synthesis Example G Synthesis of Urethane-modified Methacrylic EpoxyResin (G)

To 1100 parts by weight of trimethylolpropane, 1.6 parts by weight of3,5-dibutyl-4-hydroxytoluene as a polymerization inhibitor, 0.08 partsby weight of dibutyl tin dilaurate as a reaction catalyst, and 6080parts by weight of diphenylmethane diisocyanate were added, and areaction was performed for 2 hours under reflux with stirring at 60° C.Then, 235 parts by weight of 2-hydroxyethyl methacrylate and 910 partsby weight of glycidol were added thereto, and the reaction was performedfor 2 hours under reflux with stirring at 90° C. while air was supplied.Then, 100 parts by weight of the obtained resin was filtered through acolumn filled with 30 parts by weight of a nature-originated boundsubstance of quartz and kaolin (Sillitin V85 manufactured by HOFFMANNMINERAL GmbH) to adsorb ionic impurities in the reactant, and toluenewas removed, thereby producing a urethane-modified methacrylic epoxyresin (G).

[Production of Sealant]

Sealant (1)

With a planetary stirring machine, 85 parts by weight of the acrylicacid-modified resorcinol epoxy resin (A), 18 parts by weight of theacrylic acid-modified bisphenol A epoxy resin (B), 33 parts by weight ofthe acrylic acid-modified diphenyl ether epoxy resin (C), 10 parts byweight of 2,2-dimethoxy-1,2-diphenylethane-1-one as a photoradicalpolymerization initiator, 38 parts by weight of a hydrazido curing agentas a latent thermosetting agent (Amicure VDH manufactured by AjinomotoFine-Techno Co., Inc.), 6 parts by weight ofγ-glycidoxypropyltrimethoxysilane, 30 parts by weight of sphericalsilica (SO-C1 manufactured by Admatechs Company Limited), and 20 partsby weight of fine particles having a core-shell structure (F-351manufactured by Zeon Corporation) were mixed with each other by stirringinto an homogeneous liquid. The mixture was further subjected to mixingin a ceramic three-roll mill and then subjected to defoaming and mixingby stirring with a planetary stirring machine, thereby producing asealant (1). The sealant (1) had the following properties.

Hydrogen-bonding Functional Group Value: 4.8×10⁻³

Specific Resistance of Sealant before Curing (Ω·cm): 7.2×10⁹

Volume Resistivity of Sealant after Curing (Ω·cm): 2.6×10¹³

Sealant (2)

With a planetary stirring machine, 100 parts by weight of a phenolnovolac epoxy resin (“N-740” manufactured by DIC Corporation), 60 partsby weight of the methacrylic acid-modified bisphenol E epoxy resin (D),3 parts by weight of1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propane-1-one as aphotoradical polymerization initiator, 65 parts by weight of a hydrazidocuring agent as a latent thermosetting agent (Amicure VDH manufacturedby Ajinomoto Fine-Techno Co., Inc.), 3 parts by weight ofγ-glycidoxypropyltrimethoxysilane, 6 parts by weight of talc, and 0.5parts by weight of dibutylhydroxytoluene as an antioxidant were mixedwith each other by stirring into an homogeneous liquid. The mixture wasfurther subjected to mixing in a ceramic three-roll mill and thensubjected to defoaming and mixing by stirring with a planetary stirringmachine, thereby producing a sealant (2). The sealant (2) had thefollowing properties.

Hydrogen-bonding Functional Group Value: 3.7×10⁻³

Specific Resistance of Sealant before Curing (Ω·cm): 2.4×10⁷

Volume Resistivity of Sealant after Curing (Ω·cm): 1.3×10¹³

Sealant (3)

With a planetary stirring machine, 60 parts by weight of the acrylicacid-modified phenol novolac epoxy resin (E), 29 parts by weight of theurethane-modified acrylic epoxy resin (F), 1.5 parts by weight of2,2-diethoxyacetophenone as a photopolymerization initiator, 22 parts byweight of a hydrazido curing agent as a latent thermosetting agent(Amicure VDH manufactured by Ajinomoto Fine-Techno Co., Inc.), 1.5 partsby weight of γ-glycidoxypropyltrimethoxysilane, and 34 parts by weightof silica particles (average particle size of 1.5 μm) were mixed witheach other and stirred. The mixture was further subjected to mixing in aceramic three-roll mill and then subjected to defoaming and mixing bystirring with a planetary stirring machine, thereby producing a sealant(3). The sealant (3) had the following properties.

Hydrogen-bonding Functional Group Value: 4.3×10⁻³

Specific Resistance of Sealant before Curing (Ω·cm): 2.1×10⁹

Volume Resistivity of Sealant after Curing (Ω·cm): 1.8×10¹³

Sealant (4)

As curable resins, 35 parts by weight of the acrylic acid-modifiedbisphenol A epoxy resin (B), 30 parts by weight of acaprolactone-modified bisphenol A epoxy acrylate (“EBECRYL 3708”manufactured by DAICEL-CYTEC Company, Ltd.), and 25 parts by weight ofan acrylic acid-modified bisphenol F epoxy resin (KRM8287 manufacturedby DAICEL-CYTEC Company, Ltd.) were mixed with each other. Then, 2 partsby weight of 2,2-dimethoxy-2-phenylacetophenone as a photopolymerizationinitiator, 6 parts by weight of sebacic dihydrazide (“SDH” manufacturedby Otsuka Chemical Co., Ltd.) as a thermosetting agent, 25 parts byweight of silica (SO-C1 manufactured by Admatechs Company Limited) as afiller, 2 parts by weight of γ-glycidoxypropyltrimethoxysilane(“KBM-403” manufactured by Shin-Etsu Chemical Co., Ltd.) as a silanecoupling agent, and 17 parts by weight of fine particles of a core-shellacrylate copolymer (F351 manufactured by Gants Chemical Co., Ltd.) weremixed therewith and stirred with a planetary stirring machine. Themixture was further subjected to mixing in a ceramic three-roll mill andthen subjected to defoaming and mixing by stirring with a planetarystirring machine, thereby producing a sealant (4). The sealant (4) hadthe following properties.

Hydrogen-bonding Functional Group Value: 4.1×10⁻³

Specific Resistance of Sealant before Curing (Ω·cm): 8.9×10⁸

Volume Resistivity of Sealant after Curing (Ω·cm): 1.7×10¹³

Sealant (5)

With a planetary stirring machine, 50 parts by weight of the methacrylicacid-modified bisphenol E epoxy resin (D), 50 parts by weight of theurethane-modified methacrylic epoxy resin (G), 1.5 parts by weight of2,2-diethoxyacetophenone as a photopolymerization initiator, 18 parts byweight of a hydrazido curing agent as a latent thermosetting agent(Amicure VDH manufactured by Ajinomoto Fine-Techno Co., Inc.), 1.5 partsby weight of γ-glycidoxypropyltrimethoxysilane, and 35 parts by weightof silica particles (SO-C1 manufactured by Admatechs Company Limited)were mixed with each other and stirred. The mixture was furthersubjected to mixing in a ceramic three-roll mill and then subjected todefoaming and mixing by stirring with a planetary stirring machine,thereby producing a sealant (5). The sealant (5) had the followingproperties.

Hydrogen-bonding Functional Group Value: 3.6×10⁻³

Specific Resistance of Sealant before Curing (Ω·cm): 4.1×10⁶

Volume Resistivity of Sealant after Curing (Ω·cm): 1.1×10¹³

Comparative Sealant (C1)

A curable resin composition composed of 35 parts by weight of urethaneacrylate (AH-600 manufactured by kyoeisha Chemical Co., Ltd.), 15 partsby weight of 2-hydroxybutyl acrylate, 50 parts by weight of isobornylacrylate, and 3 parts by weight of benzophenone was prepared and stirredwith a planetary stirring machine. The composition was homogeneouslymixed in a ceramic three-roll mill to produce a photocurable comparativesealant (C1). The comparative sealant (C1) had the following properties.

Hydrogen-bonding Functional Group Value: 2.2×10⁻⁵

Specific Resistance of Sealant before Curing (Ω·cm): 6.0×10⁵

Volume Resistivity of Sealant after Curing (Ω·cm): 1.2×10¹³

Comparative Sealant (C2)

A curable resin composition composed of 50 parts by weight a bisphenol Aepoxy resin (jER828US manufactured by Mitsubishi Chemical Corporation)and 25 parts by weight of a hydrazido curing agent (NDH manufactured byJapan Hydrazine company, Inc.) was prepared and stirred with a planetarystirring machine. The composition was homogeneously mixed in a ceramicthree-roll mill to produce a comparative sealant (C2). The comparativesealant (C2) had the following properties.

Hydrogen-bonding Functional Group Value: 2.7×10⁻⁷

Specific Resistance of Sealant before Curing (Ω·cm): 5.0×10¹⁰

Volume Resistivity of Sealant after Curing (Ω·cm): 3.0×10¹³

Examples 1 to 5

A transparent electrode was formed on each of first and secondsubstrates, a black matrix (BM) was provided to the second substrate,vertical alignment films (SE-5300) wereprovided on the facing sides ofthe substrates, and then alignment treatment was carried out. Thesealants (1) to (5) were individually put into the syringes ofdispensers, defoamed, and then applied from the dispensers to thealignment-film-side surface of the first substrate in the form of arectangular frame. In a state in which the sealant was not cured, finedroplets of a liquid crystal composition 1 shown in the below table weredropped onto the entire surface of the first substrate within the frame,and the second substrate was immediately attached thereto with a vacuumbonding machine under a vacuum of 5 Pa. The conditions of theapplication of the sealant and the gap between the substrates wereadjusted to satisfy the following requirements: after the release of thevacuum, the width of the compressed sealant was approximately 1.2 mm,and 0.3-mm part of the width overlapped the BM. Then, the sealed portionwas promptly irradiated with ultraviolet emitted from a high pressuremercury lamp from the second substrate side at an intensity of 100mW/cm² for 30 seconds, and liquid crystal annealing was performed at120° C. for an hour to cause thermal curing, thereby producing VA liquidcrystal display devices of Examples 1 to 5 (d_(gap)=3.5 μm). The VHR ofeach of the liquid crystal display devices was measured. Each of theliquid crystal display devices was subjected to evaluations of unevenalignment and screen burn-in. Results of the measurement and evaluationsare shown in the below table.

TABLE 1 Liquid Crystal Composition 1 T_(NI)/° C. 81.0 Δn 0.103 Δε −2.9η/mPa · s 20.3 γ₁/mPa · s 112 γ₁/Δn² × 10⁻² 105 3-Cy-Cy-2 24%  3-Cy-Cy-410%  3-Cy-Cy-5 5% 3-Cy-Ph-O1 2% 3-Cy-Ph5-O2 13%  2-Cy-Ph-Ph5-O2 9%3-Cy-Ph-Ph5-O2 9% 3-Cy-Cy-Ph5-O3 5% 4-Cy-Cy-Ph5-O2 6% 5-Cy-Cy-Ph5-O2 5%3-Ph-Ph5-Ph-2 6% 4-Ph-Ph5-Ph-2 6%

TABLE 2 Example 1 Example 2 Example 3 Example 4 Example 5 Liquid crystalLiquid crystal Liquid crystal Liquid crystal Liquid crystal Liquidcrystal composition composition 1 composition 1 composition 1composition 1 composition 1 Sealant Sealant (1) Sealant (2) Sealant (3)Sealant (4) Sealant (5) VHR 99.6 99.2 99.5 99.3 99.1 Uneven ExcellentExcellent Excellent Excellent Good alignment Screen burn-in ExcellentExcellent Excellent Excellent Good

In the liquid crystal composition 1, the temperature range of the liquidcrystal layer was 75.8° C., which was practical for a liquid crystalcomposition used in TVs; in addition, the liquid crystal composition 1had a dielectric anisotropy with a large absolute value, low viscosity,and proper Δn.

The liquid crystal display devices of Examples 1 to 5 had a high VHR. Inthe evaluation of uneven alignment, no uneven alignment was observed, oran acceptable degree of slight uneven alignment was observed, if any. Inthe evaluation of screen burn-in, no afterimage was observed, or anacceptable degree of slight afterimage was observed, if any.

Examples 6 to 15

As in Example 1, liquid crystal compositions 2 and 3 shown in the belowtables were individually disposed between substrates, the sealants (1)to (5) were used to produce liquid crystal display devices of Examples 6to 15, and the VHRs thereof were measured. The liquid crystal displaydevices were subjected to the evaluations of uneven alignment and screenburn-in. Results of the measurement and evaluations are shown in thebelow tables.

TABLE 3 Liquid Crystal Composition 2 Liquid Crystal Composition 3T_(NI)/° C. 76.0 T_(NI)/° C. 84.8 Δn 0.103 Δn 0.103 Δε −2.9 Δε −2.9η/mPa · s 19.8 η/mPa · s 21.4 γ₁/mPa · s 110 γ₁/mPa · s 119 γ₁/Δn² ×10⁻² 103 γ₁/Δn² × 10⁻² 112 3-Cy-Cy-2 24%  3-Cy-Cy-2 24%  3-Cy-Cy-4 10% 3-Cy-Cy-4 11%  3-Cy-Ph-O1 7% 3-Cy-Ph5-O2 12%  3-Cy-Ph5-O2 14% 2-Cy-Ph-Ph5-O2 5% 2-Cy-Ph-Ph5-O2 7% 3-Cy-Ph-Ph5-O2 6% 3-Cy-Ph-Ph5-O2 9%3-Cy-Cy-Ph5-O3 8% 3-Cy-Cy-Ph5-O3 5% 4-Cy-Cy-Ph5-O2 8% 4-Cy-Cy-Ph5-O2 7%5-Cy-Cy-Ph5-O2 8% 5-Cy-Cy-Ph5-O2 5% 3-Ph-Ph5-Ph-2 6% 3-Ph-Ph5-Ph-2 6%4-Ph-Ph5-Ph-2 6% 4-Ph-Ph5-Ph-2 6% 5-Ph-Ph-1 3% 3-Cy-Cy-Ph-1 3%

TABLE 4 Example 6 Example 7 Example 8 Example 9 Example 10 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 2 composition 2 composition 2composition 2 composition 2 Sealant Sealant (1) Sealant (2) Sealant (3)Sealant (4) Sealant (5) VHR 99.5 99.1 99.3 99.2 99.1 Uneven ExcellentExcellent Excellent Excellent Good alignment Screen burn-in ExcellentExcellent Excellent Excellent Excellent

TABLE 5 Example 11 Example 12 Example 13 Example 14 Example 15 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 3 composition 3 composition 3composition 3 composition 3 Sealant Sealant (1) Sealant (2) Sealant (3)Sealant (4) Sealant (5) VHR 99.6 99.3 99.5 99.4 99.1 Uneven ExcellentExcellent Excellent Excellent Excellent alignment Screen burn-inExcellent Excellent Excellent Excellent Good

In each of the liquid crystal compositions 2 and 3, the temperaturerange of the liquid crystal layer was practical for liquid crystalcompositions used in TVs; in addition, each liquid crystal compositionhad a dielectric anisotropy with a large absolute value, low viscosity,and proper Δn.

The liquid crystal display devices of Examples 6 to 15 each had a highVHR. In the evaluation of uneven alignment, no uneven alignment wasobserved. In the evaluation of screen burn-in, no afterimage wasobserved, or an acceptable degree of slight afterimage was observed, ifany.

Examples 16 to 30

As in Example 1, liquid crystal compositions 4 to 6 shown in the belowtables were individually disposed between substrates, the sealants (1)to (5) were used to produce liquid crystal display devices of Examples16 to 30, and the VHRs thereof were measured. The liquid crystal displaydevices were subjected to the evaluations of uneven alignment and screenburn-in. Results of the measurement and evaluations are shown in thebelow tables.

TABLE 6 Liquid Crystal Composition 4 Liquid Crystal Composition 5 LiquidCrystal Composition 6 T_(NI)/° C. 74.9 T_(NI)/° C. 80.2 T_(NI)/° C. 85.7Δn 0.102 Δn 0.105 Δn 0.104 Δε −2.9 Δε −2.9 Δε −3.0 η/mPa · s 21.1 η/mPa· s 22.7 η/mPa · s 22.9 γ₁/mPa · s 116 γ₁/mPa · s 124 γ₁/mPa · s 126γ₁/Δn² × 10⁻² 111 γ₁/Δn² × 10⁻² 112 γ₁/Δn² × 10⁻² 116 3-Cy-Cy-2 22% 3-Cy-Cy-2 20%  3-Cy-Cy-2 20%  3-Cy-Cy-4 11%  3-Cy-Cy-4 10%  3-Cy-Cy-410%  3-Cy-Ph5-O2 7% 3-Cy-Ph5-O2 7% 3-Cy-Ph5-O2 7% 3-Cy-Ph5-O4 8%3-Cy-Ph5-O4 7% 3-Cy-Ph5-O4 7% 2-Cy-Ph-Ph5-O2 6% 2-Cy-Ph-Ph5-O2 6%2-Cy-Ph-Ph5-O2 6% 3-Cy-Ph-Ph5-O2 7% 3-Cy-Ph-Ph5-O2 7% 3-Cy-Ph-Ph5-O2 7%3-Cy-Cy-Ph5-O3 7% 3-Cy-Cy-Ph5-O3 7% 3-Cy-Cy-Ph5-O3 7% 4-Cy-Cy-Ph5-O2 7%4-Cy-Cy-Ph5-O2 8% 4-Cy-Cy-Ph5-O2 8% 5-Cy-Cy-Ph5-O2 7% 5-Cy-Cy-Ph5-O2 7%5-Cy-Cy-Ph5-O2 7% 3-Ph-Ph5-Ph-2 4% 3-Ph-Ph5-Ph-2 4% 3-Ph-Ph5-Ph-2 4%4-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2 4% 5-Ph-Ph-1 8%5-Ph-Ph-1 8% 5-Ph-Ph-1 5% 3-Cy-Cy-Ph-1 2% 3-Cy-Cy-Ph-1 5% 3-Cy-Cy-Ph-18%

TABLE 7 Example 16 Example 17 Example 18 Example 19 Example 20 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 4 composition 4 composition 4composition 4 composition 4 Sealant Sealant (1) Sealant (2) Sealant (3)Sealant (4) Sealant (5) VHR 99.6 99.2 99.5 99.3 99.0 Uneven ExcellentExcellent Excellent Excellent Good alignment Screen burn-in ExcellentExcellent Excellent Excellent Good

TABLE 8 Example 21 Example 22 Example 23 Example 24 Example 25 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 5 composition 5 composition 5composition 5 composition 5 Sealant Sealant (1) Sealant (2) Sealant (3)Sealant (4) Sealant (5) VHR 99.5 99.3 99.5 99.4 99.2 Uneven ExcellentGood Excellent Excellent Excellent alignment Screen burn-in ExcellentExcellent Excellent Excellent Excellent

TABLE 9 Example 26 Example 27 Example 28 Example 29 Example 30 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 6 composition 6 composition 6composition 6 composition 6 Sealant Sealant (1) Sealant (2) Sealant (3)Sealant (4) Sealant (5) VHR 99.6 99.3 99.4 99.4 99.1 Uneven ExcellentGood Excellent Excellent Excellent alignment Screen burn-in ExcellentExcellent Excellent Excellent Good

In each of the liquid crystal compositions 4 to 6, the temperature rangeof the liquid crystal layer was practical for liquid crystalcompositions used in TVs; in addition, each liquid crystal compositionhad a dielectric anisotropy with a large absolute value, low viscosity,and proper Δn.

The liquid crystal display devices of Examples 16 to 30 each had a highVHR. In the evaluation of uneven alignment, no uneven alignment wasobserved, or an acceptable degree of slight uneven alignment wasobserved, if any. In the evaluation of screen burn-in, no afterimage wasobserved, or an acceptable degree of slight afterimage was observed, ifany.

Examples 31 to 45

As in Example 1, liquid crystal compositions 7 to 9 shown in the belowtables were individually disposed between substrates, the sealants (1)to (5) were used to produce liquid crystal display devices of Examples31 to 45, and the VHRs thereof were measured. The liquid crystal displaydevices were subjected to the evaluations of uneven alignment and screenburn-in. Results of the measurement and evaluations are shown in thebelow tables.

TABLE 10 Liquid Crystal Liquid Crystal Liquid Crystal Composition 7Composition 8 Composition 9 T_(NI)/° C. 75.1 T_(NI)/° C. 80.4 T_(NI)/°C. 85.1 Δn 0.103 Δn 0.103 Δn 0.103 Δε −2.6 Δε −2.6 Δε −2.6 η/mPa · s20.5 η/mPa · s 21.6 η/mPa · s 22.7 γ₁/mPa · s 117 γ₁/mPa · s 125 γ₁/mPa· s 130 γ₁/Δn² × 10⁻² 110 γ₁/Δn² × 10⁻² 117 γ₁/Δn² × 10⁻² 122 3-Cy-Cy-215%  3-Cy-Cy-2 15%  3-Cy-Cy-2 10%  3-Cy-Cy-4 12%  3-Cy-Cy-4 12% 3-Cy-Cy-4 15%  3-Cy-Cy-5 7% 3-Cy-Cy-5 7% 3-Cy-Cy-5 12%  3-Cy-Ph-O1 12% 3-Cy-Ph-O1 12%  3-Cy-Ph-O1 9% 3-Cy-Ph5-O2 6% 3-Cy-Ph5-O2 5% 3-Cy-Ph5-O25% 3-Cy-Ph5-O4 7% 3-Cy-Ph5-O4 5% 3-Cy-Ph5-O4 5% 2-Cy-Ph-Ph5-O2 11% 2-Cy-Ph-Ph5-O2 11%  2-Cy-Ph-Ph5-O2 11%  3-Cy-Ph-Ph5-O2 12% 3-Cy-Ph-Ph5-O2 11%  3-Cy-Ph-Ph5-O2 11%  3-Cy-Cy-Ph5-O3 3% 3-Cy-Cy-Ph5-O34% 3-Cy-Cy-Ph5-O3 4% 4-Cy-Cy-Ph5-O2 4% 4-Cy-Cy-Ph5-O2 6% 4-Cy-Cy-Ph5-O26% 5-Cy-Cy-Ph5-O2 3% 5-Cy-Cy-Ph5-O2 4% 5-Cy-Cy-Ph5-O2 4% 3-Ph-Ph5-Ph-24% 3-Ph-Ph5-Ph-2 4% 3-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2 4%4-Ph-Ph5-Ph-2 4%

TABLE 11 Example 31 Example 32 Example 33 Example 34 Example 35 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 7 composition 7 composition 7composition 7 composition 7 Sealant Sealant (1) Sealant (2) Sealant (3)Sealant (4) Sealant (5) VHR 99.5 99.3 99.5 99.4 99.0 Uneven ExcellentExcellent Excellent Excellent Good alignment Screen burn-in ExcellentExcellent Excellent Excellent Good

TABLE 12 Example 36 Example 37 Example 38 Example 39 Example 40 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 8 composition 8 composition 8composition 8 composition 8 Sealant Sealant (1) Sealant (2) Sealant (3)Sealant (4) Sealant (5) VHR 99.6 99.3 99.5 99.3 99.1 Uneven ExcellentExcellent Excellent Excellent Excellent alignment Screen burn-inExcellent Good Excellent Excellent Good

TABLE 13 Example 41 Example 42 Example 43 Example 44 Example 45 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 9 composition 9 composition 9composition 9 composition 9 Sealant Sealant (1) Sealant (2) Sealant (3)Sealant (4) Sealant (5) VHR 99.4 99.1 99.4 99.2 99.0 Uneven ExcellentGood Excellent Excellent Good alignment Screen burn-in ExcellentExcellent Excellent Excellent Good

In each of the liquid crystal compositions 7 to 9, the temperature rangeof the liquid crystal layer was practical for liquid crystalcompositions used in TVs; in addition, each liquid crystal compositionhad a dielectric anisotropy with a large absolute value, low viscosity,and proper Δn.

The liquid crystal display devices of Examples 31 to 45 each had a highVHR. In the evaluation of uneven alignment, no uneven alignment wasobserved, or an acceptable degree of slight uneven alignment wasobserved, if any. In the evaluation of screen burn-in, no afterimage wasobserved, or an acceptable degree of slight afterimage was observed, ifany.

Examples 46 to 60

As in Example 1, liquid crystal compositions 10 to 12 shown in the belowtables were individually disposed between substrates, the sealants (1)to (5) were used to produce liquid crystal display devices of Examples46 to 60, and the VHRs thereof were measured. The liquid crystal displaydevices were subjected to the evaluations of uneven alignment and screenburn-in. Results of the measurement and evaluations are shown in thebelow tables.

TABLE 14 Liquid Crystal Liquid Crystal Liquid Crystal Composition 10Composition 11 Composition 12 T_(NI)/° C. 76.7 T_(NI)/° C. 80.3 T_(NI)/°C. 85.8 Δn 0.109 Δn 0.105 Δn 0.104 Δε −3.0 Δε −3.1 Δε −3.2 η/mPa · s22.4 η/mPa · s 21.8 η/mPa · s 22.0 γ₁/mPa · s 131 γ₁/mPa · s 126 γ₁/mPa· s 128 γ₁/Δn² × 10⁻² 110 γ₁/Δn² × 10⁻² 114 γ₁/Δn² × 10⁻² 119 3-Cy-Cy-224%  3-Cy-Cy-2 24%  3-Cy-Cy-2 24%  3-Cy-Cy-4 6% 3-Cy-Cy-4 10%  3-Cy-Cy-410%  3-Cy-Ph-O1 5% 3-Cy-Ph-O1 4% 3-Cy-Ph-O1 4% 3-Cy-Ph5-O4 6%3-Cy-Ph5-O4 6% 3-Cy-Ph5-O4 6% 3-Ph-Ph5-O2 6% 3-Ph-Ph5-O2 6% 3-Ph-Ph5-O26% 2-Cy-Ph-Ph5-O2 8% 2-Cy-Ph-Ph5-O2 8% 2-Cy-Ph-Ph5-O2 8% 3-Cy-Ph-Ph5-O28% 3-Cy-Ph-Ph5-O2 8% 3-Cy-Ph-Ph5-O2 8% 3-Cy-Cy-Ph5-O3 7% 3-Cy-Cy-Ph5-O37% 3-Cy-Cy-Ph5-O3 7% 4-Cy-Cy-Ph5-O2 9% 4-Cy-Cy-Ph5-O2 9% 4-Cy-Cy-Ph5-O29% 5-Cy-Cy-Ph5-O2 7% 5-Cy-Cy-Ph5-O2 7% 5-Cy-Cy-Ph5-O2 7% 3-Ph-Ph5-Ph-24% 3-Ph-Ph5-Ph-2 4% 3-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2 4%4-Ph-Ph5-Ph-2 4% 5-Ph-Ph-1 6% 5-Ph-Ph-1 3% 3-Cy-Cy-Ph-1 3%

TABLE 15 Example 46 Example 47 Example 48 Example 49 Example 50 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 10 composition 10 composition 10composition 10 composition 10 Sealant Sealant (1) Sealant (2) Sealant(3) Sealant (4) Sealant (5) VHR 99.7 99.4 99.6 99.5 99.2 UnevenExcellent Excellent Excellent Excellent Excellent alignment Screenburn-in Excellent Excellent Excellent Excellent Excellent

TABLE 16 Example 51 Example 52 Example 53 Example 54 Example 55 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 11 composition 11 composition 11composition 11 composition 11 Sealant Sealant (1) Sealant (2) Sealant(3) Sealant (4) Sealant (5) VHR 99.4 99.2 99.3 99.2 89.9 UnevenExcellent Excellent Excellent Good Good alignment Screen burn-inExcellent Good Excellent Excellent Good

TABLE 17 Example 56 Example 57 Example 58 Example 59 Example 60 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 12 composition 12 composition 12composition 12 composition 12 Sealant Sealant (1) Sealant (2) Sealant(3) Sealant (4) Sealant (5) VHR 99.5 99.2 99.5 99.3 99.1 UnevenExcellent Excellent Excellent Excellent Excellent alignment Screenburn-in Excellent Excellent Excellent Excellent Good

In each of the liquid crystal compositions 10 to 12, the temperaturerange of the liquid crystal layer was practical for liquid crystalcompositions used in TVs; in addition, each liquid crystal compositionhad a dielectric anisotropy with a large absolute value, low viscosity,and proper Δn.

The liquid crystal display devices of Examples 46 to 60 each had a highVHR. In the evaluation of uneven alignment, no uneven alignment wasobserved, or an acceptable degree of slight uneven alignment wasobserved, if any. In the evaluation of screen burn-in, no afterimage wasobserved, or an acceptable degree of slight afterimage was observed, ifany.

Examples 61 to 75

As in Example 1, liquid crystal compositions 13 to 15 shown in the belowtables were individually disposed between substrates, the sealants (1)to (5) were used to produce liquid crystal display devices of Examples61 to 75, and the VHRs thereof were measured. The liquid crystal displaydevices were subjected to the evaluations of uneven alignment and screenburn-in. Results of the measurement and evaluations are shown in thebelow tables.

TABLE 18 Liquid Crystal Liquid Crystal Liquid Crystal Composition 13Composition 14 Composition 15 T_(NI)/° C. 71.9 T_(NI)/° C. 78.8 T_(NI)/°C. 73.8 Δn 0.116 Δn 0.113 Δn 0.113 Δε −3.6 Δε −3.5 Δε −3.9 η/mPa · s21.2 η/mPa · s 21.1 η/mPa · s 21.8 γ₁/mPa · s 123 γ₁/mPa · s 122 γ₁/mPa· s 123 γ₁/Δn² × 10⁻² 92 γ₁/Δn² × 10⁻² 95 γ₁/Δn² × 10⁻² 97 3-Cy-Cy-224%  3-Cy-Cy-2 23%  3-Cy-Cy-2 16%  3-Cy-Ph-O1 7% 3-Cy-Cy-4 5% 3-Cy-Cy-49% 2-Cy-Ph5-O2 6% 3-Cy-Ph-O1 3% 3-Cy-Ph-O1 6% 3-Cy-Ph5-O4 6% 2-Cy-Ph5-O25% 2-Cy-Ph5-O2 6% 3-Ph-Ph5-O2 5% 3-Cy-Ph5-O4 5% 3-Cy-Ph5-O4 6%5-Ph-Ph5-O2 5% 3-Ph-Ph5-O2 5% 3-Ph-Ph5-O2 6% 2-Cy-Ph-Ph5-O2 7%5-Ph-Ph5-O2 5% 5-Ph-Ph5-O2 6% 3-Cy-Ph-Ph5-O2 9% 2-Cy-Ph-Ph5-O2 7%2-Cy-Ph-Ph5-O2 5% 3-Cy-Cy-Ph5-O3 5% 3-Cy-Ph-Ph5-O2 7% 3-Cy-Ph-Ph5-O2 7%4-Cy-Cy-Ph5-O2 5% 3-Cy-Cy-Ph5-O3 5% 3-Cy-Cy-Ph5-O3 5% 5-Cy-Cy-Ph5-O2 4%4-Cy-Cy-Ph5-O2 6% 4-Cy-Cy-Ph5-O2 6% 3-Ph-Ph5-Ph-2 5% 5-Cy-Cy-Ph5-O2 5%5-Cy-Cy-Ph5-O2 6% 4-Ph-Ph5-Ph-2 6% 3-Ph-Ph5-Ph-2 5% 3-Ph-Ph5-Ph-2 5%3-Cy-Cy-Ph-1 6% 4-Ph-Ph5-Ph-2 6% 4-Ph-Ph5-Ph-2 5% 3-Cy-Cy-Ph-1 8%3-Cy-Cy-Ph-1 6%

TABLE 19 Example 61 Example 62 Example 63 Example 64 Example 65 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 13 composition 13 composition 13composition 13 composition 13 Sealant Sealant (1) Sealant (2) Sealant(3) Sealant (4) Sealant (5) VHR 99.6 99.4 99.5 99.4 90.2 UnevenExcellent Excellent Excellent Excellent Excellent alignment Screenburn-in Excellent Excellent Excellent Excellent Good

TABLE 20 Example 66 Example 67 Example 68 Example 69 Example 70 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 14 composition 14 composition 14composition 14 composition 14 Sealant Sealant (1) Sealant (2) Sealant(3) Sealant (4) Sealant (5) VHR 99.5 99.2 99.4 99.4 99.1 UnevenExcellent Excellent Excellent Excellent Good alignment Screen burn-inExcellent Excellent Excellent Excellent Good

TABLE 21 Example 71 Example 72 Example 73 Example 74 Example 75 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 15 composition 15 composition 15composition 15 composition 15 Sealant Sealant (1) Sealant (2) Sealant(3) Sealant (4) Sealant (5) VHR 99.5 99.1 99.4 99.3 89.9 UnevenExcellent Excellent Excellent Excellent Good alignment Screen burn-inExcellent Good Excellent Excellent Good

In each of the liquid crystal compositions 13 to 15, the temperaturerange of the liquid crystal layer was practical for liquid crystalcompositions used in TVs; in addition, each liquid crystal compositionhad a dielectric anisotropy with a large absolute value, low viscosity,and proper Δn.

The liquid crystal display devices of Examples 61 to 75 each had a highVHR. In the evaluation of uneven alignment, no uneven alignment wasobserved, or an acceptable degree of slight uneven alignment wasobserved, if any. In the evaluation of screen burn-in, no afterimage wasobserved, or an acceptable degree of slight afterimage was observed, ifany.

Examples 76 to 90

As in Example 1, liquid crystal compositions 16 to 18 shown in the belowtables were individually disposed between substrates, the sealants (1)to (5) were used to produce liquid crystal display devices of Examples76 to 90, and the VHRs thereof were measured. The liquid crystal displaydevices were subjected to the evaluations of uneven alignment and screenburn-in. Results of the measurement and evaluations are shown in thebelow tables.

TABLE 22 Liquid Crystal Liquid Crystal Liquid Crystal Composition 16Composition 17 Composition 18 T_(NI)/° C. 75.9 T_(NI)/° C. 82.3 T_(NI)/°C. 85.7 Δn 0.112 Δn 0.111 Δn 0.112 Δε −2.8 Δε −2.7 Δε −2.8 η/mPa · s19.8 η/mPa · s 19.2 η/mPa · s 20.1 γ₁/mPa · s 121 γ₁/mPa · s 114 γ₁/mPa· s 119 γ₁/Δn² × 10⁻² 96 γ₁/Δn² × 10⁻² 94 γ₁/Δn² × 10⁻² 95 3-Cy-Cy-219%  3-Cy-Cy-2 21%  3-Cy-Cy-2 19%  3-Cy-Cy-4 12%  3-Cy-Cy-4 12% 3-Cy-Cy-4 12%  3-Cy-Cy-5 5% 3-Cy-Cy-5 5% 3-Cy-Cy-5 4% 3-Cy-Ph-O1 5%2-Cy-Ph5-O2 4% 2-Cy-Ph5-O2 4% 2-Cy-Ph5-O2 4% 3-Cy-Ph5-O4 4% 3-Cy-Ph5-O44% 3-Cy-Ph5-O4 4% 3-Ph-Ph5-O2 3% 3-Ph-Ph5-O2 3% 3-Ph-Ph5-O2 3%5-Ph-Ph5-O2 4% 5-Ph-Ph5-O2 4% 5-Ph-Ph5-O2 4% 2-Cy-Ph-Ph5-O2 6%2-Cy-Ph-Ph5-O2 6% 2-Cy-Ph-Ph5-O2 6% 3-Cy-Ph-Ph5-O2 6% 3-Cy-Ph-Ph5-O2 6%3-Cy-Ph-Ph5-O2 6% 3-Cy-Cy-Ph5-O3 5% 3-Cy-Cy-Ph5-O3 5% 3-Cy-Cy-Ph5-O3 5%4-Cy-Cy-Ph5-O2 5% 4-Cy-Cy-Ph5-O2 5% 4-Cy-Cy-Ph5-O2 5% 5-Cy-Cy-Ph5-O2 4%5-Cy-Cy-Ph5-O2 4% 5-Cy-Cy-Ph5-O2 5% 3-Ph-Ph5-Ph-2 7% 3-Ph-Ph5-Ph-2 7%3-Ph-Ph5-Ph-2 8% 4-Ph-Ph5-Ph-2 8% 4-Ph-Ph5-Ph-2 8% 4-Ph-Ph5-Ph-2 9%3-Cy-Cy-Ph-1 6% 3-Cy-Cy-Ph-1 9%

TABLE 23 Example 76 Example 77 Example 78 Example 79 Example 80 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 16 composition 16 composition 16composition 16 composition 16 Sealant Sealant (1) Sealant (2) Sealant(3) Sealant (4) Sealant (5) VHR 99.6 99.4 99.5 99.4 99.2 UnevenExcellent Excellent Excellent Excellent Excellent alignment Screenburn-in Excellent Excellent Excellent Excellent Good

TABLE 24 Example 81 Example 82 Example 83 Example 84 Example 85 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 17 composition 17 composition 17composition 17 composition 17 Sealant Sealant (1) Sealant (2) Sealant(3) Sealant (4) Sealant (5) VHR 99.5 99.2 99.5 99.3 99.0 UnevenExcellent Excellent Excellent Excellent Good alignment Screen burn-inExcellent Excellent Excellent Excellent Good

TABLE 25 Example 86 Example 87 Example 88 Example 89 Example 90 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 18 composition 18 composition 18composition 18 composition 18 Sealant Sealant (1) Sealant (2) Sealant(3) Sealant (4) Sealant (5) VHR 99.4 99.1 99.3 99.3 99.0 UnevenExcellent Good Excellent Excellent Excellent alignment Screen burn-inExcellent Excellent Excellent Excellent Good

In each of the liquid crystal compositions 16 to 18, the temperaturerange of the liquid crystal layer was practical for liquid crystalcompositions used in TVs; in addition, each liquid crystal compositionhad a dielectric anisotropy with a large absolute value, low viscosity,and proper Δn.

The liquid crystal display devices of Examples 76 to 90 each had a highVHR. In the evaluation of uneven alignment, no uneven alignment wasobserved, or an acceptable degree of slight uneven alignment wasobserved, if any. In the evaluation of screen burn-in, no afterimage wasobserved, or an acceptable degree of slight afterimage was observed, ifany.

Examples 91 to 105

As in Example 1, liquid crystal compositions 19 to 21 shown in the belowtables were individually disposed between substrates, the sealants (1)to (5) were used to produce liquid crystal display devices of Examples91 to 105, and the VHRs thereof were measured. The liquid crystaldisplay devices were subjected to the evaluations of uneven alignmentand screen burn-in. Results of the measurement and evaluations are shownin the below tables.

TABLE 26 Liquid Crystal Liquid Crystal Liquid Crystal Composition 19Composition 20 Composition 21 T_(NI)/°C. 77.1 T_(NI)/° C. 82.7 T_(NI)/°C. 86.4 Δn 0.104 Δn 0.107 Δn 0.106 Δε −3.5 Δε −3.0 Δε −3.0 η/mPa · s25.1 η/mPa · s 24.2 η/mPa · s 24.4 γ₁/mPa · s 141 γ₁/mPa · s 141 γ₁/mPa· s 142 γ₁/Δn² × 10⁻² 131 γ₁/Δn² × 10⁻² 123 γ₁/Δn² × 10⁻² 126 3-Cy-Cy-222%  3-Cy-Cy-2 24%  3-Cy-Cy-2 24%  3-Cy-Ph-O1 14%  3-Cy-Cy-4 5%3-Cy-Cy-4 5% 2-Cy-Ph5-O2 7% 3-Cy-Ph-O1 6% 3-Cy-Ph-O1 6% 3-Cy-Ph5-O4 8%2-Cy-Ph5-O2 5% 2-Cy-Ph5-O2 5% 2-Cy-Ph-Ph5-O2 7% 3-Cy-Ph5-O4 5%3-Cy-Ph5-O4 5% 3-Cy-Ph-Ph5-O2 9% 2-Cy-Ph-Ph5-O2 7% 2-Cy-Ph-Ph5-O2 7%3-Cy-Cy-Ph5-O3 8% 3-Cy-Ph-Ph5-O2 9% 3-Cy-Ph-Ph5-O2 9% 4-Cy-Cy-Ph5-O2 8%3-Cy-Cy-Ph5-O3 8% 3-Cy-Cy-Ph5-O3 8% 5-Cy-Cy-Ph5-O2 8% 4-Cy-Cy-Ph5-O2 8%4-Cy-Cy-Ph5-O2 8% 3-Ph-Ph5-Ph-2 5% 5-Cy-Cy-Ph5-O2 8% 5-Cy-Cy-Ph5-O2 8%4-Ph-Ph5-Ph-2 4% 3-Ph-Ph5-Ph-2 5% 3-Ph-Ph5-Ph-2 5% 4-Ph-Ph5-Ph-2 5%4-Ph-Ph5-Ph-2 5% 5-Ph-Ph-1 5% 5-Ph-Ph-1 3% 3-Cy-Cy-Ph-1 2%

TABLE 27 Example 91 Example 92 Example 93 Example 94 Example 95 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 19 composition 19 composition 19composition 19 composition 19 Sealant Sealant (1) Sealant (2) Sealant(3) Sealant (4) Sealant (5) VHR 99.6 99.4 99.5 99.4 99.2 UnevenExcellent Excellent Excellent Excellent Excellent alignment Screenburn-in Excellent Excellent Excellent Excellent Good

TABLE 28 Example 96 Example 97 Example 98 Example 99 Example 100 Liquidcrystal Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal composition composition 20 composition 20 composition 20composition 20 composition 20 Sealant Sealant (1) Sealant (2) Sealant(3) Sealant (4) Sealant (5) VHR 99.7 99.3 99.5 99.5 99.2 UnevenExcellent Excellent Excellent Excellent Excellent alignment Screenburn-in Excellent Excellent Excellent Excellent Excellent

TABLE 29 Example 101 Example 102 Example 103 Example 104 Example 105Liquid crystal Liquid crystal Liquid crystal Liquid crystal Liquidcrystal Liquid crystal composition composition 21 composition 21composition 21 composition 21 composition 21 Sealant Sealant (1) Sealant(2) Sealant (3) Sealant (4) Sealant (5) VHR 99.5 99.2 99.5 99.3 99.0Uneven Excellent Excellent Excellent Excellent Good alignment Screenburn-in Excellent Good Excellent Excellent Good

In each of the liquid crystal compositions 19 to 21, the temperaturerange of the liquid crystal layer was practical for liquid crystalcompositions used in TVs; in addition, each liquid crystal compositionhad a dielectric anisotropy with a large absolute value, low viscosity,and proper Δn.

The liquid crystal display devices of Examples 91 to 105 each had a highVHR. In the evaluation of uneven alignment, no uneven alignment wasobserved, or an acceptable degree of slight uneven alignment wasobserved, if any. In the evaluation of screen burn-in, no afterimage wasobserved, or an acceptable degree of slight afterimage was observed, ifany.

Examples 106 to 120

As in Example 1, liquid crystal compositions 22 to 24 shown in the belowtables were individually disposed between substrates, the sealants (1)to (5) were used to produce liquid crystal display devices of Examples106 to 120, and the VHRs thereof were measured. The liquid crystaldisplay devices were subjected to the evaluations of uneven alignmentand screen burn-in. Results of the measurement and evaluations are shownin the below tables.

TABLE 30 Liquid Crystal Liquid Crystal Liquid Crystal Composition 22Composition 23 Composition 24 T_(NI)/°C. 75.5 T_(NI)/° C. 80.3 T_(NI)/°C. 85.0 Δn 0.102 Δn 0.101 Δn 0.102 Δε −2.8 Δε −2.9 Δε −3.0 η/mPa · s22.2 η/mPa · s 22.0 η/mPa · s 22.7 γ₁/mPa · s 121 γ₁/mPa · s 118 γ₁/mPa· s 122 γ₁/Δn² × 10⁻² 117 γ₁/Δn² × 10⁻² 117 γ₁/Δn² × 10⁻² 118 3-Cy-Cy-214%  3-Cy-Cy-2 17%  3-Cy-Cy-2 16%  3-Cy-Cy-4 12%  3-Cy-Cy-4 12% 3-Cy-Cy-4 12%  3-Cy-Cy-5 5% 3-Cy-Cy-5 5% 3-Cy-Cy-5 5% 3-Cy-Ph-O1 7%3-Cy-Ph-O1 6% 3-Cy-Ph-O1 5% 2-Cy-Ph5-O2 7% 2-Cy-Ph5-O2 12%  2-Cy-Ph5-O212%  3-Cy-Ph5-O4 7% 2-Cy-Ph-Ph5-O2 9% 2-Cy-Ph-Ph5-O2 9% 2-Cy-Ph-Ph5-O28% 3-Cy-Ph-Ph5-O2 9% 3-Cy-Ph-Ph5-O2 9% 3-Cy-Ph-Ph5-O2 8% 3-Cy-Cy-Ph5-O36% 3-Cy-Cy-Ph5-O3 6% 3-Cy-Cy-Ph5-O3 6% 4-Cy-Cy-Ph5-O2 8% 4-Cy-Cy-Ph5-O28% 4-Cy-Cy-Ph5-O2 7% 5-Cy-Cy-Ph5-O2 6% 5-Cy-Cy-Ph5-O2 6% 5-Cy-Cy-Ph5-O26% 3-Ph-Ph5-Ph-2 3% 3-Ph-Ph5-Ph-2 3% 3-Ph-Ph5-Ph-2 3% 4-Ph-Ph5-Ph-2 3%4-Ph-Ph5-Ph-2 3% 4-Ph-Ph5-Ph-2 3% 5-Ph-Ph-1 4% 5-Ph-Ph-1 3% 5-Ph-Ph-1 6%3-Cy-Cy-Ph-1 3% 3-Cy-Cy-Ph-1 1%

TABLE 31 Example 106 Example 107 Example 108 Example 109 Example 110Liquid crystal Liquid crystal Liquid crystal Liquid crystal Liquidcrystal Liquid crystal composition composition 22 composition 22composition 22 composition 22 composition 22 Sealant Sealant (1) Sealant(2) Sealant (3) Sealant (4) Sealant (5) VHR 99.4 99.2 99.4 99.3 99.0Uneven Excellent Excellent Excellent Excellent Excellent alignmentScreen burn-in Excellent Excellent Excellent Excellent Good

TABLE 32 Example 111 Example 112 Example 113 Example 114 Example 115Liquid crystal Liquid crystal Liquid crystal Liquid crystal Liquidcrystal Liquid crystal composition composition 23 composition 23composition 23 composition 23 composition 23 Sealant Sealant (1) Sealant(2) Sealant (3) Sealant (4) Sealant (5) VHR 99.5 99.3 99.4 99.4 99.2Uneven Excellent Excellent Excellent Excellent Excellent alignmentScreen burn-in Excellent Excellent Excellent Excellent Excellent

TABLE 33 Example 116 Example 117 Example 118 Example 119 Example 120Liquid crystal Liquid crystal Liquid crystal Liquid crystal Liquidcrystal Liquid crystal composition composition 24 composition 24composition 24 composition 24 composition 24 Sealant Sealant (1) Sealant(2) Sealant (3) Sealant (4) Sealant (5) VHR 99.6 99.3 99.5 99.4 99.2Uneven Excellent Excellent Excellent Excellent Good alignment Screenburn-in Excellent Excellent Excellent Excellent Good

In each of the liquid crystal compositions 22 to 24, the temperaturerange of the liquid crystal layer was practical for liquid crystalcompositions used in TVs; in addition, each liquid crystal compositionhad a dielectric anisotropy with a large absolute value, low viscosity,and proper Δn.

The liquid crystal display devices of Examples 106 to 120 each had ahigh VHR. In the evaluation of uneven alignment, no uneven alignment wasobserved, or an acceptable degree of slight uneven alignment wasobserved, if any. In the evaluation of screen burn-in, no afterimage wasobserved, or an acceptable degree of slight afterimage was observed, ifany.

Examples 121 to 135

As in Example 1, liquid crystal compositions 25 to 27 shown in the belowtables were individually disposed between substrates, the sealants (1)to (5) were used to produce liquid crystal display devices of Examples121 to 135, and the VHRs thereof were measured. The liquid crystaldisplay devices were subjected to the evaluations of uneven alignmentand screen burn-in. Results of the measurement and evaluations are shownin the below tables.

TABLE 34 Liquid Crystal Liquid Crystal Liquid Crystal Composition 25Composition 26 Composition 27 T_(NI)/°C. 75.6 T_(NI)/° C. 81.1 T_(NI)/°C. 85.7 Δn 0.104 Δn 0.105 Δn 0.105 Δε −2.8 Δε −2.8 Δε −2.9 η/mPa · s20.2 η/mPa · s 20.8 η/mPa · s 21.0 γ₁/mPa · s 117 γ₁/mPa · s 119 γ₁/mPa· s 92 γ₁/Δn² × 10⁻² 107 γ₁/Δn² × 10⁻² 107 γ₁/Δn² × 10⁻² 82 3-Cy-Cy-225%  3-Cy-Cy-2 25%  3-Cy-Cy-2 25%  3-Cy-Cy-4 10%  3-Cy-Cy-4 10% 3-Cy-Cy-4 12%  3-Cy-Ph-O1 4% 3-Cy-Ph-O1 4% 2-Cy-Ph5-O2 12%  2-Cy-Ph5-O27% 2-Cy-Ph5-O2 12%  2-Cy-Ph-Ph5-O2 5% 3-Cy-Ph5-O4 8% 2-Cy-Ph-Ph5-O2 5%3-Cy-Ph-Ph5-O2 6% 2-Cy-Ph-Ph5-O2 5% 3-Cy-Ph-Ph5-O2 6% 3-Cy-Cy-Ph5-O3 7%3-Cy-Ph-Ph5-O2 6% 3-Cy-Cy-Ph5-O3 7% 4-Cy-Cy-Ph5-O2 8% 3-Cy-Cy-Ph5-O3 6%4-Cy-Cy-Ph5-O2 8% 5-Cy-Cy-Ph5-O2 7% 4-Cy-Cy-Ph5-O2 7% 5-Cy-Cy-Ph5-O2 7%3-Ph-Ph5-Ph-2 8% 5-Cy-Cy-Ph5-O2 6% 3-Ph-Ph5-Ph-2 8% 4-Ph-Ph5-Ph-2 8%3-Ph-Ph5-Ph-2 8% 4-Ph-Ph5-Ph-2 8% 3-Cy-Cy-Ph-1 2% 4-Ph-Ph5-Ph-2 8%

TABLE 35 Example 121 Example 122 Example 123 Example 124 Example 125Liquid crystal Liquid crystal Liquid crystal Liquid crystal Liquidcrystal Liquid crystal composition composition 25 composition 25composition 25 composition 25 composition 25 Sealant Sealant (1) Sealant(2) Sealant (3) Sealant (4) Sealant (5) VHR 99.6 99.3 99.5 99.4 99.1Uneven Excellent Excellent Excellent Excellent Excellent alignmentScreen burn-in Excellent Excellent Excellent Excellent Good

TABLE 36 Example 126 Example 127 Example 128 Example 129 Example 130Liquid crystal Liquid crystal Liquid crystal Liquid crystal Liquidcrystal Liquid crystal composition composition 26 composition 26composition 26 composition 26 composition 26 Sealant Sealant (1) Sealant(2) Sealant (3) Sealant (4) Sealant (5) VHR 99.5 99.2 99.5 99.4 99.0Uneven Excellent Excellent Excellent Excellent Excellent alignmentScreen burn-in Excellent Excellent Excellent Excellent Good

TABLE 37 Example 131 Example 132 Example 133 Example 134 Example 135Liquid crystal Liquid crystal Liquid crystal Liquid crystal Liquidcrystal Liquid crystal composition composition 27 composition 27composition 27 composition 27 composition 27 Sealant Sealant (1) Sealant(2) Sealant (3) Sealant (4) Sealant (5) VHR 99.4 99.1 99.3 99.3 99.0Uneven Excellent Excellent Excellent Excellent Good alignment Screenburn-in Excellent Excellent Excellent Excellent Good

In each of the liquid crystal compositions 25 to 27, the temperaturerange of the liquid crystal layer was practical for liquid crystalcompositions used in TVs; in addition, each liquid crystal compositionhad a dielectric anisotropy with a large absolute value, low viscosity,and proper Δn.

The liquid crystal display devices of Examples 121 to 135 each had ahigh VHR. In the evaluation of uneven alignment, no uneven alignment wasobserved, or an acceptable degree of slight uneven alignment wasobserved, if any. In the evaluation of screen burn-in, no afterimage wasobserved, or an acceptable degree of slight afterimage was observed, ifany.

Examples 136 to 140

To the liquid crystal composition 1, 0.3 mass % of 2-methyl-acrylic acid4-{2-[4-(2-acryloyloxy-ethyl)-phenoxycarbonyl]-ethyl}-biphenyl-4′-ylester was added to produce a liquid crystal composition 28. As inExample 1, the liquid crystal composition 28 was disposed between thesubstrates and then confined with use of the sealants (1) to (5). In astate in which a driving voltage was applied between the electrodes,ultraviolet was radiated thereto for 600 seconds (3.0 J/cm²) forpolymerization, thereby producing PSVA liquid crystal display devices ofExamples 136 to 140. The VHRs of the liquid crystal display devices weremeasured; in addition, the liquid crystal display devices were subjectedto evaluations of uneven alignment and screen burn-in. Results of themeasurement and evaluations are shown in the below table.

TABLE 38 Example 136 Example 137 Example 138 Example 139 Example 140Liquid crystal Liquid crystal Liquid crystal Liquid crystal Liquidcrystal Liquid crystal composition composition 28 composition 28composition 28 composition 28 composition 28 Sealant Sealant (1) Sealant(2) Sealant (3) Sealant (4) Sealant (5) VHR 99.6 99.4 99.5 99.5 99.2Uneven Excellent Excellent Excellent Excellent Excellent alignmentScreen burn-in Excellent Excellent Excellent Excellent Good

The liquid crystal display devices of Examples 136 to 140 each had ahigh VHR. In the evaluation of uneven alignment, no uneven alignment wasobserved. In the evaluation of screen burn-in, no afterimage wasobserved, or an acceptable degree of slight afterimage was observed, ifany.

Examples 141 to 145

To the liquid crystal composition 13, 0.3 mass % of bismethacrylic acidbiphenyl-4,4′-diyl ester was added to produce a liquid crystalcomposition 29. As in Example 1, the liquid crystal composition 29 wasdisposed between the substrates and then confined with use of thesealants (1) to (5). In a state in which a driving voltage was appliedbetween the electrodes, ultraviolet was radiated thereto for 600 seconds(3.0 J/cm²) for polymerization, thereby producing PSVA liquid crystaldisplay devices of Examples 141 to 145. The VHRs of the liquid crystaldisplay devices were measured; in addition, the liquid crystal displaydevices were subjected to evaluations of uneven alignment and screenburn-in. Results of the measurement and evaluations are shown in thebelow table.

TABLE 39 Example 141 Example 142 Example 143 Example 144 Example 145Liquid Liquid crystal Liquid crystal Liquid crystal Liquid crystalLiquid crystal crystal composition 29 composition 29 compositioncomposition composition composition 29 29 29 Sealant Sealant (1) Sealant(2) Sealant (3) Sealant (4) Sealant (5) VHR 99.4 99.2 99.3 99.3 99.1Uneven Excellent Excellent Excellent Excellent Excellent alignmentScreen Excellent Excellent Excellent Excellent Good burn-in

The liquid crystal display devices of Examples 141 to 145 each had ahigh VHR. In the evaluation of uneven alignment, no uneven alignment wasobserved. In the evaluation of screen burn-in, no afterimage wasobserved, or an acceptable degree of slight afterimage was observed, ifany.

Examples 146 to 150

To the liquid crystal composition 19, 0.3 mass % of bismethacrylic acid3-fluorobiphenyl-4,4′-diyl was added to produce a liquid crystalcomposition 30. As in Example 1, the liquid crystal composition 30 wasdisposed between the substrates and then confined with use of thesealants (1) to (5). In a state in which a driving voltage was appliedbetween electrodes, ultraviolet was radiated thereto for 600 seconds(3.0 J/cm²) for polymerization, thereby producing PSVA liquid crystaldisplay devices of Examples 146 to 150. The VHRs of the liquid crystaldisplay devices were measured; in addition, the liquid crystal displaydevices were subjected to evaluations of uneven alignment and screenburn-in. Results of the measurement and evaluations are shown in thebelow table.

TABLE 40 Example 146 Example 147 Example 148 Example 149 Example 150Liquid crystal Liquid crystal Liquid crystal Liquid crystal Liquidcrystal Liquid crystal composition composition 30 composition 30composition 30 composition 30 composition 30 Sealant Sealant (1) Sealant(2) Sealant (3) Sealant (4) Sealant (5) VHR 99.6 99.4 99.5 99.4 99.2Uneven Excellent Excellent Excellent Excellent Good alignment Screenburn-in Excellent Excellent Excellent Excellent Good

The liquid crystal display devices of Examples 146 to 150 each had ahigh VHR. In the evaluation of uneven alignment, no uneven alignment wasobserved, or an acceptable degree of slight uneven alignment wasobserved, if any. In the evaluation of screen burn-in, no afterimage wasobserved, or an acceptable degree of slight afterimage was observed, ifany.

Examples 151 to 165

As in Example 1, liquid crystal compositions 31 to 33 shown in the belowtables were individually disposed between substrates, the sealants (1)to (5) were used to produce liquid crystal display devices of Examples151 to 165, and the VHRs thereof were measured. The liquid crystaldisplay devices were subjected to the evaluations of uneven alignmentand screen burn-in. Results of the measurement and evaluations are shownin the below tables.

TABLE 41 Liquid Crystal Liquid Crystal Liquid Crystal Composition 31Composition 32 Composition 33 TNI/° C. 75.5 TNI/° C. 75.4 TNI/° C. 83.1Δn 0.103 Δn 0.109 Δn 0.114 Δε −3.1 Δε −3.1 Δε −2.9 η/mPa · s 15.8 η/mPa· s 14.9 η/mPa · s 14.8 γ1/mPa · s 113 γ1/mPa · s 110 γ1/mPa · s 92γ1/Δn2 × 10−2 113 γ1/Δn2 × 10−2 92 γ1/Δn2 × 10−2 71 3-Cy-Cy-2 13% 2-Cy-Cy-V1 20% V2-Ph-Ph-1 5% 3-Cy-Cy-V1 12%  3-Cy-Cy-V1 13% 3-Cy-Cy-V39%  3-Cy-Cy-4 5% 3-Ph-Ph-1 10% 3-Cy-1O-Ph5-O2 5% 3-Ph-Ph-1 3% 5-Ph-Ph-1 5% 2-Cy-Cy-1O-Ph5-O2 11%  5-Ph-Ph-1 12%  3-Cy-Ph-Ph-2  6%3-Cy-Cy-1O-Ph5-O1 11%  3-Cy-Cy-Ph-1 3% 1V-Cy-1O-Ph5-O2  8%3-Cy-Cy-1O-Ph5-O2 6% V-Cy-Ph-Ph-3 6% 2-Cy-Cy-1O-Ph5-O2 10%2-Cy-Ph-Ph5-O2 6% 3-Cy-1O-Ph5-O2 11%  3-Cy-Cy-1O-Ph5-O2 10%3-Ph-Ph5-Ph-1 8% 2-Cy-Cy-1O-Ph5-O2 12%  V-Cy-Cy-1O-Ph5-O2 10%3-Ph-Ph5-Ph-2 9% 3-Cy-Cy-1O-Ph5-O2 12%  1V-Cy-Cy-1O-Ph5-O2  4%4-Cy-Cy-1O-Ph5-O2 2% 3-Ph-Ph5-Ph-2  4% V-Cy-Cy-1O-Ph5-O2 3%1V-Cy-Cy-1O-Ph5-O2 6%

TABLE 42 Example 151 Example 152 Example 153 Example 154 Example 155Liquid crystal Liquid crystal Liquid crystal Liquid crystal Liquidcrystal Liquid crystal composition composition 31 composition 31composition 31 composition 31 composition 31 Sealant Sealant (1) Sealant(2) Sealant (3) Sealant (4) Sealant (5) VHR 99.5 99.1 99.3 99.3 99.0Uneven Excellent Excellent Excellent Excellent Good alignment Screenburn-in Excellent Excellent Excellent Excellent Good

TABLE 43 Example 156 Example 157 Example 158 Example 159 Example 160Liquid crystal Liquid crystal Liquid crystal Liquid crystal Liquidcrystal Liquid crystal composition composition 32 composition 32composition 32 composition 32 composition 32 Sealant Sealant (1) Sealant(2) Sealant (3) Sealant (4) Sealant (5) VHR 99.6 99.3 99.5 99.5 99.2Uneven Excellent Excellent Excellent Excellent Excellent alignmentScreen burn-in Excellent Excellent Excellent Excellent Good

TABLE 44 Example 161 Example 162 Example 163 Example 164 Example 165Liquid crystal Liquid crystal Liquid crystal Liquid crystal Liquidcrystal Liquid crystal composition composition 33 composition 33composition 33 composition 33 composition 33 Sealant Sealant (1) Sealant(2) Sealant (3) Sealant (4) Sealant (5) VHR 99.6 99.3 99.4 99.3 99.0Uneven Excellent Excellent Excellent Excellent Good alignment Screenburn-in Excellent Good Excellent Excellent Good

The liquid crystal display devices of Examples 151 to 165 each had ahigh VHR. In the evaluation of uneven alignment, no uneven alignment wasobserved, or an acceptable degree of slight uneven alignment wasobserved, if any. In the evaluation of screen burn-in, no afterimage wasobserved, or an acceptable degree of slight afterimage was observed, ifany.

Comparative Examples 1 to 15

Except that comparative liquid crystal compositions 1 to 3 shown in thebelow tables were used in place of the liquid crystal composition 1 inExample 1, VA liquid crystal display devices of Comparative Examples 1to 15 were produced as in Example 1, and the VHRs thereof were measured.The liquid crystal display devices were subjected to the evaluations ofuneven alignment and screen burn-in. Results of the measurement andevaluations are shown in the below tables.

TABLE 45 Comparative Liquid Comparative Liquid Comparative LiquidCrystal Composition 1 Crystal Composition 2 Crystal Composition 3T_(NI)/° C. 75.5 T_(NI)/° C. 80.7 T_(NI)/° C. 85.8 Δn 0.104 Δn 0.104 Δn0.104 Δε −2.88 Δε −2.88 Δε −2.95 η/mPa · s 22.5 η/mPa · s 22.3 η/mPa · s22.4 γ₁/mPa · s 123 γ₁/mPa · s 122 γ₁/mPa · s 124 γ₁/Δn² × 10⁻² 114γ₁/Δn² × 10⁻² 113 γ₁/Δn² × 10⁻² 114 3-Cy-Cy-2 24%  3-Cy-Cy-2 24% 3-Cy-Cy-2 24%  3-Cy-Cy-4 4% 3-Cy-Cy-4 4% 3-Cy-Cy-4 4% 3-Cy-Ph5-O2 7%3-Cy-Ph5-O2 7% 3-Cy-Ph5-O2 7% 3-Cy-Ph5-O4 8% 3-Cy-Ph5-O4 8% 3-Cy-Ph5-O48% 2-Cy-Ph-Ph5-O2 4% 2-Cy-Ph-Ph5-O2 5% 2-Cy-Ph-Ph5-O2 6% 3-Cy-Ph-Ph5-O25% 3-Cy-Ph-Ph5-O2 6% 3-Cy-Ph-Ph5-O2 7% 3-Cy-Cy-Ph5-O3 8% 3-Cy-Cy-Ph5-O37% 3-Cy-Cy-Ph5-O3 7% 4-Cy-Cy-Ph5-O2 10%  4-Cy-Cy-Ph5-O2 9%4-Cy-Cy-Ph5-O2 7% 5-Cy-Cy-Ph5-O2 8% 5-Cy-Cy-Ph5-O2 7% 5-Cy-Cy-Ph5-O2 7%3-Ph-Ph5-Ph-2 4% 3-Ph-Ph5-Ph-2 4% 3-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2 4%4-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2 4% 5-Ph-Ph-1 10%  5-Ph-Ph-1 7% 5-Ph-Ph-14% 3-Cy-Cy-Ph-1 4% 3-Cy-Cy-Ph-1 8% 3-Cy-Cy-Ph-1 11% 

TABLE 46 Comparative Comparative Comparative Comparative ComparativeExample1 Example 2 Example 3 Example 4 Example 5 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 1 composition 1 composition 1 composition 1composition 1 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 98.0 97.5 97.8 97.6 97.3 Uneven Bad Poor Bad Bad Pooralignment Screen burn-in Bad Poor Poor Poor Poor

TABLE 47 Comparative Comparative Comparative Comparative ComparativeExample 6 Example 7 Example 8 Example 9 Example 10 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 2 composition 2 composition 2 composition 2composition 2 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 98.1 97.6 97.8 97.7 97.4 Uneven Bad Poor Bad Poor Pooralignment Screen burn-in Bad Poor Poor Poor Poor

TABLE 48 Comparative Comparative Comparative Comparative ComparativeExample 11 Example 12 Example 13 Example 14 Example 15 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 3 composition 3 composition 3 composition 3composition 3 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 98.1 97.5 97.8 97.7 97.2 Uneven Bad Poor Poor Poor Pooralignment Screen burn-in Bad Poor Bad Poor Poor

Each of the liquid crystal display devices of Comparative Examples 1 to15 had a lower VHR than the liquid crystal display device of the presentinvention. In the evaluation of uneven alignment, an unacceptable degreeof uneven alignment was observed. Furthermore, also in the evaluation ofscreen burn-in, an unacceptable degree of afterimages was observed.

Comparative Examples 16 to 30

Except that comparative liquid crystal compositions 4 to 6 shown in thebelow tables were used in place of the comparative liquid crystalcomposition 1, VA liquid crystal display devices of Comparative Examples16 to 30 were produced as in Comparative Example 1, and the VHRs thereofwere measured. The liquid crystal display devices were subjected to theevaluations of uneven alignment and screen burn-in. Results of themeasurement and evaluations are shown in the below tables.

TABLE 49 Comparative Liquid Comparative Liquid Comparative LiquidCrystal Composition 4 Crystal Composition 5 Crystal Composition 6T_(NI)/° C. 73.6 T_(NI)/° C. 80.9 T_(NI)/° C. 84.7 Δn 0.099 Δn 0.094 Δn0.085 Δε −2.15 Δε −2.16 Δε −2.13 η/mPa · s 17.7 η/mPa · s 17.0 η/mPa · s17.5 γ₁/mPa · s 104 γ₁/mPa · s 97 γ₁/mPa · s 98 γ₁/Δn² × 10⁻² 106 γ₁/Δn²× 10⁻² 109 γ₁/Δn² × 10⁻² 136 3-Cy-Cy-2 20%  3-Cy-Cy-2 24%  3-Cy-Cy-221%  3-Cy-Cy-4 12%  3-Cy-Cy-4 12%  3-Cy-Cy-4 15%  3-Cy-Cy-5 7% 3-Cy-Cy-515%  3-Cy-Cy-5 15%  3-Cy-Ph-O1 12%  3-Cy-Ph5-O2 5% 3-Cy-Ph5-O2 5%3-Cy-Ph5-O2 5% 3-Cy-Ph5-O4 5% 3-Cy-Ph5-O4 5% 3-Cy-Ph5-O4 5%2-Cy-Ph-Ph5-O2 11%  2-Cy-Ph-Ph5-O2 4% 2-Cy-Ph-Ph5-O2 11%  3-Cy-Ph-Ph5-O211%  3-Cy-Ph-Ph5-O2 5% 3-Cy-Ph-Ph5-O2 11%  3-Cy-Cy-Ph5-O3 3%3-Cy-Cy-Ph5-O3 7% 3-Cy-Cy-Ph5-O3 3% 4-Cy-Cy-Ph5-O2 3% 4-Cy-Cy-Ph5-O2 8%4-Cy-Cy-Ph5-O2 3% 5-Cy-Cy-Ph5-O2 3% 5-Cy-Cy-Ph5-O2 7% 5-Cy-Cy-Ph5-O2 3%3-Ph-Ph5-Ph-2 4% 3-Ph-Ph5-Ph-2 4% 3-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2 4%4-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2 4%

TABLE 50 Comparative Comparative Comparative Comparative ComparativeExample 16 Example 17 Example 18 Example 19 Example 20 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 4 composition 4 composition 4 composition 4composition 4 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 98.0 97.5 97.8 97.6 97.1 Uneven Bad Poor Poor Poor Pooralignment Screen burn-in Bad Poor Bad Bad Poor

TABLE 51 Comparative Comparative Comparative Comparative ComparativeExample 21 Example 22 Example 23 Example 24 Example 25 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 5 composition 5 composition 5 composition 5composition 5 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 98.1 97.5 97.8 97.6 97.2 Uneven Bad Poor Bad Poor Pooralignment Screen burn-in Bad Poor Bad Poor Poor

TABLE 52 Comparative Comparative Comparative Comparative ComparativeExample 26 Example 27 Example 28 Example 29 Example 30 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 6 composition 6 composition 6 composition 6composition 6 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 97.9 97.4 97.7 97.6 97.1 Uneven Bad Poor Bad Poor Pooralignment Screen burn-in Bad Poor Bad Poor Poor

Each of the liquid crystal display devices of Comparative Examples 16 to30 had a lower VHR than the liquid crystal display device of the presentinvention. In the evaluation of uneven alignment, an unacceptable degreeof uneven alignment was observed. Furthermore, also in the evaluation ofscreen burn-in, an unacceptable degree of afterimages was observed.

Comparative Examples 31 to 45

Except that comparative liquid crystal compositions 7 to 9 shown in thebelow tables were used in place of the comparative liquid crystalcomposition 1, VA liquid crystal display devices of Comparative Examples31 to 45 were produced as in Comparative Example 1, and the VHRs thereofwere measured. The liquid crystal display devices were subjected to theevaluations of uneven alignment and screen burn-in. Results of themeasurement and evaluations are shown in the below tables.

TABLE 53 Comparative Liquid Comparative Liquid Comparative LiquidCrystal Composition 7 Crystal Composition 8 Crystal Composition 9T_(NI)/° C. 77.1 T_(NI)/° C. 80.8 T_(NI)/° C. 86.3 Δn 0.109 Δn 0.108 Δn0.107 Δε −2.10 Δε −2.20 Δε −2.27 η/mPa · s 21.6 η/mPa · s 22.1 η/mPa · s22.3 γ₁/mPa · s 130 γ₁/mPa · s 133 γ₁/mPa · s 134 γ₁/Δn² × 10⁻² 109γ₁/Δn² × 10⁻² 114 γ₁/Δn² × 10⁻² 118 3-Cy-Cy-2 24%  3-Cy-Cy-2 24% 3-Cy-Cy-2 24%  3-Cy-Cy-4 7% 3-Cy-Cy-4 7% 3-Cy-Cy-4 7% 3-Cy-Ph-O1 5%3-Cy-Ph-O1 5% 3-Cy-Ph-O1 5% 2-Cy-Ph5-O2 2% 2-Cy-Ph5-O2 2% 2-Cy-Ph5-O2 2%3-Cy-Ph5-O4 2% 3-Cy-Ph5-O4 2% 3-Cy-Ph5-O4 2% 2-Cy-Ph-Ph5-O2 8%2-Cy-Ph-Ph5-O2 8% 2-Cy-Ph-Ph5-O2 8% 3-Cy-Ph-Ph5-O2 8% 3-Cy-Ph-Ph5-O2 8%3-Cy-Ph-Ph5-O2 8% 3-Cy-Cy-Ph5-O3 7% 3-Cy-Cy-Ph5-O3 8% 3-Cy-Cy-Ph5-O3 8%4-Cy-Cy-Ph5-O2 9% 4-Cy-Cy-Ph5-O2 8% 4-Cy-Cy-Ph5-O2 8% 5-Cy-Cy-Ph5-O2 7%5-Cy-Cy-Ph5-O2 8% 5-Cy-Cy-Ph5-O2 8% 3-Ph-Ph5-Ph2 4% 3-Ph-Ph5-Ph-2 4%3-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2 4%5-Ph-Ph-1 13%  5-Ph-Ph-1 11%  5-Ph-Ph-1 8% 3-Cy-Cy-Ph-1 1% 3-Cy-Cy-Ph-14%

TABLE 54 Comparative Comparative Comparative Comparative ComparativeExample 31 Example 32 Example 33 Example 34 Example 35 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 7 composition 7 composition 7 composition 7composition 7 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 97.7 97.1 97.5 97.4 96.8 Uneven Bad Poor Bad Poor Pooralignment Screen burn-in Bad Poor Poor Poor Poor

TABLE 55 Comparative Comparative Comparative Comparative ComparativeExample 36 Example 37 Example 38 Example 39 Example 40 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 8 composition 8 composition 8 composition 8composition 8 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 98.0 97.4 97.8 97.6 97.1 Uneven Bad Poor Poor Poor Pooralignment Screen burn-in Bad Poor Bad Poor Poor

TABLE 56 Comparative Comparative Comparative Comparative ComparativeExample 41 Example 42 Example 43 Example 44 Example 45 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 9 composition 9 composition 9 composition 9composition 9 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 98.1 97.5 97.9 97.7 97.3 Uneven Bad Poor Bad Poor Pooralignment Screen burn-in Bad Poor Bad Poor Poor

Each of the liquid crystal display devices of Comparative Examples 31 to45 had a lower VHR than the liquid crystal display device of the presentinvention. In the evaluation of uneven alignment, an unacceptable degreeof uneven alignment was observed. Furthermore, also in the evaluation ofscreen burn-in, an unacceptable degree of afterimages was observed.

Comparative Examples 46 to 55

Except that comparative liquid crystal compositions 10 and 11 shown inthe below tables were used in place of the comparative liquid crystalcomposition 1, VA liquid crystal display devices of Comparative Examples46 to 55 were produced as in Comparative Example 1, and the VHRs thereofwere measured. The liquid crystal display devices were subjected to theevaluations of uneven alignment and screen burn-in. Results of themeasurement and evaluations are shown in the below tables.

TABLE 57 Comparative Comparative Liquid Crystal Liquid CrystalComposition 10 Composition 11 T_(NI)/° C. 62.2 T_(NI)/° C. 72.4 Δn 0.087Δn 0.088 Δε −4.1 Δε −4.2 η/mPa · s 21.3 η/mPa · s 23.8 γ₁/mPa · s 97γ₁/mPa · s 106 γ₁/Δn² × 10⁻² 129 γ₁/Δn² × 10⁻² 138 3-Cy-Cy-2 12% 3-Cy-Cy-4 20%  3-Cy-Cy-4 12%  3-Cy-Cy-5 15%  3-Cy-Cy-5 5% 2-Cy-Ph5-O216%  3-Cy-Ph-O1 6% 3-Cy-Ph5-O4 16%  2-Cy-Ph5-O2 16%  2-Cy-Ph-Ph5-O2 7%3-Cy-Ph5-O4 16%  3-Cy-Ph-Ph5-O2 8% 2-Cy-Ph-Ph5-O2 7% 3-Cy-Cy-Ph5-O3 5%3-Cy-Ph-Ph5-O2 8% 4-Cy-Cy-Ph5-O2 5% 3-Cy-Cy-Ph5-O3 5% 5-Cy-Cy-Ph5-O2 5%4-Cy-Cy-Ph5-O2 5% 3-Cy-Cy-Ph-1 3% 5-Cy-Cy-Ph5-O2 5% 3-Cy-Cy-Ph-1 3%

TABLE 58 Comparative Comparative Comparative Comparative ComparativeExample 46 Example 47 Example 48 Example 49 Example 50 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 10 composition 10 composition 10 composition 10composition 10 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 98.2 97.5 98.0 97.8 97.2 Uneven Bad Poor Bad Poor Pooralignment Screen burn-in Bad Poor Bad Bad Poor

TABLE 59 Comparative Comparative Comparative Comparative ComparativeExample 51 Example 52 Example 53 Example 54 Example 55 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 11 composition 11 composition 11 composition 11composition 11 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 97.9 97.2 97.7 97.5 96.9 Uneven Bad Poor Bad Poor Pooralignment Screen burn-in Bad Poor Bad Poor Poor

Each of the liquid crystal display devices of Comparative Examples 46 to55 had a lower VHR than the liquid crystal display device of the presentinvention. In the evaluation of uneven alignment, an unacceptable degreeof uneven alignment was observed. Furthermore, also in the evaluation ofscreen burn-in, an unacceptable degree of afterimages was observed.

Comparative Examples 56 to 70

Except that comparative liquid crystal compositions 12 to 14 shown inthe below tables were used in place of the comparative liquid crystalcomposition 1, VA liquid crystal display devices of Comparative Examples56 to 70 were produced as in Comparative Example 1, and the VHRs thereofwere measured. The liquid crystal display devices were subjected to theevaluations of uneven alignment and screen burn-in. Results of themeasurement and evaluations are shown in the below tables.

TABLE 60 Comparative Comparative Comparative Liquid Crystal LiquidCrystal Liquid Crystal Composition 12 Composition 13 Composition 14T_(NI)/° C. 74.9 T_(NI)/° C. 79.6 T_(NI)/° C. 85.4 Δn 0.103 Δn 0.104 Δn0.107 Δε −2.34 Δε −2.39 Δε −2.46 η/mPa · s 18.4 η/mPa · s 18.9 η/mPa · s20.0 γ₁/mPa · s 106 γ₁/mPa · s 108 γ₁/mPa · s 114 γ₁/Δn² × 10⁻² 99γ₁/Δn² × 10⁻² 99 γ₁/Δn² × 10⁻² 99 3-Cy-Cy-2 20%  3-Cy-Cy-2 20% 3-Cy-Cy-2 18%  3-Cy-Cy-4 12%  3-Cy-Cy-4 12%  3-Cy-Cy-4 12%  3-Cy-Cy-5 5%3-Cy-Cy-5 5% 3-Cy-Cy-5 5% 3-Cy-Ph-O1 5% 3-Cy-Ph-O1 2% 2-Cy-Ph5-O2 7%2-Cy-Ph5-O2 7% 2-Cy-Ph5-O2 7% 3-Cy-Ph5-O4 8% 3-Cy-Ph5-O4 8% 3-Cy-Ph5-O48% 2-Cy-Ph-Ph5-O2 6% 2-Cy-Ph-Ph5-O2 6% 2-Cy-Ph-Ph5-O2 6% 3-Cy-Ph-Ph5-O26% 3-Cy-Ph-Ph5-O2 6% 3-Cy-Ph-Ph5-O2 6% 3-Cy-Cy-Ph5-O3 4% 3-Cy-Cy-Ph5-O34% 3-Cy-Cy-Ph5-O3 4% 4-Cy-Cy-Ph5-O2 4% 4-Cy-Cy-Ph5-O2 4% 4-Cy-Cy-Ph5-O24% 5-Cy-Cy-Ph5-O2 4% 5-Cy-Cy-Ph5-O2 4% 5-Cy-Cy-Ph5-O2 4% 3-Ph-Ph5-Ph-27% 3-Ph-Ph5-Ph-2 7% 3-Ph-Ph5-Ph-2 7% 4-Ph-Ph5-Ph-2 8% 4-Ph-Ph5-Ph-2 8%4-Ph-Ph5-Ph-2 8% 3-Cy-Cy-Ph-1 11%  3-Cy-Cy-Ph-1 4% 3-Cy-Cy-Ph-1 7%

TABLE 61 Comparative Comparative Comparative Comparative ComparativeExample 56 Example 57 Example 58 Example 59 Example 60 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 12 composition 12 composition 12 composition 12composition 12 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 97.8 97.3 97.6 97.4 96.9 Uneven Poor Poor Poor Poor Pooralignment Screen burn-in Bad Poor Bad Poor Poor

TABLE 62 Comparative Comparative Comparative Comparative ComparativeExample 61 Example 62 Example 63 Example 64 Example 65 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 13 composition 13 composition 13 composition 13composition 13 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 97.9 97.4 97.7 97.7 97.2 Uneven Bad Poor Poor Poor Pooralignment Screen burn-in Bad Poor Bad Poor Poor

TABLE 63 Comparative Comparative Comparative Comparative ComparativeExample 66 Example 67 Example 68 Example 69 Example 70 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 14 composition 14 composition 14 composition 14composition 14 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 98.0 97.3 97.8 97.6 97.0 Uneven Bad Poor Bad Poor Pooralignment Screen burn-in Bad Poor Bad Poor Poor

Each of the liquid crystal display devices of Comparative Examples 56 to70 had a lower VHR than the liquid crystal display device of the presentinvention. In the evaluation of uneven alignment, an unacceptable degreeof uneven alignment was observed. Furthermore, also in the evaluation ofscreen burn-in, an unacceptable degree of afterimages was observed.

Comparative Examples 71 and 75

Except that a comparative liquid crystal composition 15 shown in thebelow table was used in place of the comparative liquid crystalcomposition 1, VA liquid crystal display devices of Comparative Examples71 and 75 were produced as in Comparative Example 1, and the VHRsthereof were measured. The liquid crystal display devices were subjectedto the evaluations of uneven alignment and screen burn-in. Results ofthe measurement and evaluations are shown in the below tables.

TABLE 64 Comparative Liquid Crystal Composition 12 T_(NI)/° C. 86.3 Δn0.105 Δε −3.41 η/mPa · s 26.4 γ₁/mPa · s 149 γ₁/Δn² × 10⁻² 135 3-Cy-Cy-224% 3-Cy-Ph-O1 11% 2-Cy-Ph5-O2 10% 2-Cy-Ph-Ph5-O2  7% 3-Cy-Ph-Ph5-O2  9%3-Cy-Cy-Ph5-O3 10% 4-Cy-Cy-Ph5-O2 10% 5-Cy-Cy-Ph5-O2 10% 3-Ph-Ph5-Ph-2 4% 4-Ph-Ph5-Ph-2  4% 5-Ph-Ph-1  1%

TABLE 65 Comparative Comparative Comparative Comparative ComparativeExample 71 Example 72 Example 73 Example 74 Example 75 Liquid crystalComparative Comparative Comparative Comparative Comparative compositionliquid crystal liquid crystal liquid crystal liquid crystal liquidcrystal composition 15 composition 15 composition 15 composition 15composition 15 Sealant Sealant (1) Sealant (2) Sealant (3) Sealant (4)Sealant (5) VHR 97.9 97.4 97.8 97.6 97.2 Uneven Bad Poor Bad Poor Pooralignment Screen burn-in Bad Poor Poor Poor Poor

Comparative Examples 76 to 91

Except that the sealants used in Examples 1, 6, 36, 61, 66, 91, 96, and126 were changed to comparative sealants (C1) and (C2), VA liquidcrystal display devices of Comparative Examples 76 to 91 were similarlyproduced, and the VHRs thereof were measured. The liquid crystal displaydevices were subjected to the evaluations of uneven alignment and screenburn-in. Results of the measurement and evaluations are shown in thebelow tables.

TABLE 66 Comparative Comparative Comparative Comparative Example 76Example 77 Example 78 Example 79 Liquid crystal Liquid Liquid LiquidLiquid composition crystal crystal crystal crystal compositioncomposition composition composition 1 2 8 13 Sealant ComparativeComparative Comparative Comparative sealant (C1) sealant (C1) sealant(C1) sealant (C1) VHR 98.1 98.0 97.4 97.5 Uneven Poor Bad Poor Pooralignment Screen burn-in Bad Poor Poor Poor

TABLE 67 Comparative Comparative Comparative Comparative Example 80Example 81 Example 82 Example 83 Liquid crystal Liquid Liquid LiquidLiquid composition crystal crystal crystal crystal compositioncomposition composition composition 14 19 20 26 Sealant ComparativeComparative Comparative Comparative sealant (C1) sealant (C1) sealant(C1) sealant (C1) VHR 97.7 97.6 97.6 97.4 Uneven Poor Poor Poor Pooralignment Screen burn-in Poor Poor Poor Poor

TABLE 68 Comparative Comparative Comparative Comparative Example 84Example 85 Example 86 Example 87 Liquid crystal Liquid Liquid LiquidLiquid composition crystal crystal crystal crystal compositioncomposition composition composition 1 2 8 13 Sealant ComparativeComparative Comparative Comparative sealant (C2) sealant (C2) sealant(C2) sealant (C2) VHR 97.6 97.6 97.3 97.4 Uneven Bad Poor Poor Pooralignment Screen burn-in Poor Poor Poor Poor

TABLE 69 Comparative Comparative Comparative Comparative Example 88Example 89 Example 90 Example 91 Liquid crystal Liquid Liquid LiquidLiquid composition crystal crystal crystal crystal compositioncomposition composition composition 14 19 20 26 Sealant ComparativeComparative Comparative Comparative sealant (C2) sealant (C2) sealant(C2) sealant (C2) VHR 97.5 97.4 97.3 97.1 Uneven Poor Poor Poor Pooralignment Screen burn-in Poor Poor Poor Poor

Each of the liquid crystal display devices of Comparative Examples 76 to91 had a lower VHR than the liquid crystal display device of the presentinvention. In the evaluation of uneven alignment, an unacceptable degreeof uneven alignment was observed. Furthermore, also in the evaluation ofscreen burn-in, an unacceptable degree of afterimages was observed.

The invention claimed is:
 1. A liquid crystal display device comprisinga first substrate, a second substrate, a liquid crystal layer containinga liquid crystal composition and disposed between the first and secondsubstrates, and a cured product of a curable resin composition which iscured by being exposed to an energy ray or heat, the first and secondsubstrates being attached to each other by the cured product, whereinthe liquid crystal composition contains 30 to 50% of a compoundrepresented by General Formula (I)

(where R¹ and R² each independently represent an alkyl group having 1 to8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxygroup having 1 to 8 carbon atoms, or an alkenyloxy group having 2 to 8carbon atoms; and A represents a 1,4-phenylene group or atrans-1,4-cyclohexylene group), 5 to 30% of a compound represented byGeneral Formula (II-1)

(where R³ represents an alkyl group having 1 to 8 carbon atoms, analkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1to 8carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms; R⁴represents an alkyl group having 1 to 8 carbon atoms, an alkenylgrouphaving 4 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms,or an alkenyloxy group having 3 to 8 carbon atoms; and Z³ represents asingle bond, —CH═CH—, —C≡C—, —CH₂CH₂—, —(CH₂)₄—, —COO—, —OCO—, —OCH₂—,—CH₂O—, —OCF₂—, or —CF₂O—), and 25 to 45% of a compound represented byGeneral Formula (II-2)

(where R⁵ represents an alkyl group having 1 to 8 carbon atoms, analkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1to 8carbon atoms, or an alkenyloxy group having 2to 8 carbon atoms; R⁶represents an alkyl group having 1 to 8 carbon atoms, an alkenyl grouphaving 4 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms,or an alkenyloxy group having 3 to 8 carbon atoms; B represents a1,4-phenylene group or trans-1,4-cyclohexylene group which is optionallysubstituted with a fluorine atom; Z⁴ represents a single bond, —CH═CH—,—C≡C—, —CH₂CH₂—, —(CH₂)₄—, —COO—, —OCO—, —OCH₂—, —CH₂O—, —OCF₂—, or—CF₂O—); and the curable resin composition contains a compound having atleast one (meth)acrylic group and at least one epoxy group per molecule,wherein the curable resin composition has a hydrogen-bonding functionalgroup value from 3×10⁻³ to 5×10⁻³ mol/g wherein the curable resincomposition has a volume resistivity of not less than 1×10¹³ Ω·cm aftercuring.
 2. The liquid crystal display device according to claim 1,wherein the curable resin composition contains a polymerizationinitiator.
 3. The liquid crystal display device according to claim 2,wherein the polymerization initiator is a photopolymerization initiatorand/or a thermal polymerization initiator.
 4. The liquid crystal displaydevice according to claim 1, wherein the curable resin compositioncontains a silane coupling agent.
 5. The liquid crystal display deviceaccording to claim 1, wherein the curable resin composition contains afiller.
 6. The liquid crystal display device according to claim 1,wherein the compound having at least one (meth)acrylic group and atleast one epoxy group per molecule is a (meth)acrylic acid-modifiedepoxy resin and/or a urethane-modified (meth)acrylic epoxy resin.
 7. Theliquid crystal display device according to claim 1, wherein the curableresin composition contains a resin having a (meth)acryloyloxy groupand/or a resin having an epoxy group.
 8. The liquid crystal displaydevice according to claim 1, wherein the equivalent ratio of the(meth)acrylic group to the epoxy group in the curable resin compositionis in the range of 40:60 to 95:5.
 9. The liquid crystal display deviceaccording to claim 1, wherein the curable resin composition containsfine resin particles.
 10. The liquid crystal display device according toclaim 1, wherein the liquid crystal composition layer further contains 3to 35% of a compound represented by General Formula (III)

(where R⁷ and R⁸ each independently represent an alkyl group having 1 to8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxygroup having 1 to 8 carbon atoms, or an alkenyloxy group having 2 to 8carbon atoms; D, E, and F each independently represent a 1,4-phenylenegroup or trans-1,4-cyclohexylene group which is optionally substitutedwith a fluorine atom; Z² represents a single bond, —OCH₂—, —OCO—,—CH₂O—, or —COO—; n represents 0, 1, or 2; and the compound representedby General Formula (III) excludes the compounds represented by GeneralFormulae (I), (II-1), and (II-2)).
 11. The liquid crystal display deviceaccording to claim 1, wherein at least one compound represented byGeneral Formula (I) in which A represents a trans-1,4-cyclohexylenegroup and at least one compound represented by General Formula (I) inwhich A represents a 1,4-phenylene group are used.
 12. The liquidcrystal display device according to claim 1, wherein at least onecompound represented by General Formula (II-2) in which B represents a1,4-phenylene group and at least one compound represented by GeneralFormula (II-2) in which B represents a trans-1,4-cyclohexylene group areused.
 13. The liquid crystal display device according to claim 10,wherein the amount of the compounds represented by General Formulae(II-1), (II-2), and (III) is in the range of 35 to 70%.
 14. The liquidcrystal display device according to claim 1, wherein in the liquidcrystal composition contained in the liquid crystal composition layer, Zobtained from the below equation is not more than 13000Z=γ1/Δn ² (where γ1 represents rotational viscosity, and Δn representsrefractive index anisotropy), γ1 is not more than 150, and Δn is in therange of 0.08 to 0.13.
 15. The liquid crystal display device accordingto claim 1, wherein the upper limit of the temperature of the nematicliquid crystal phase of the liquid crystal composition contained in theliquid crystal composition layer is in the range of 60 to 120° C, thelower limit is not more than −20° C., and the difference between theupper limit and the lower limit is from 100 to
 150. 16. The liquidcrystal display device according to claim 1, wherein the specificresistance of the liquid crystal composition contained in the liquidcrystal composition layer is not less than 10¹² (Ω·m).
 17. The liquidcrystal display device according to claim 1, wherein the liquid crystalcomposition layer is a polymer formed through polymerization of theliquid crystal composition further containing a polymerizable compoundrepresented by General Formula (V)

(where X¹ and X² each independently represent a hydrogen atom or amethyl group; Sp¹ and Sp² each independently represent a single bond, analkylene group having 1 to 8 carbon atoms, or —O—(CH₂)_(s)— (where srepresents an integer from 2 to 7, and the oxygen atom is bonded to anaromatic ring); Z¹ represents —OCH₂—, —CH₂O—, —COO—, —OCO—, —CF₂O—,—OCF₂—, —CH₂CH₂—, —CF₂CF₂—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—,—OCO—CH═CH—, —COO—CH₂CH₂—, —OCO—CH₂CH₂—, —CH₂CH₂—COO—, —CH₂CH₂—OCO—,—COO—CH₂—, —OCO—CH₂—, —CH₂—COO—, —CH₂—OCO—, —CY¹═CY²— (where Y¹ and Y²each independently represent a fluorine atom or a hydrogen atom), —C≡C—,or a single bond; and C represents a 1,4-phenylene group, atrans-1,4-cyclohexylene group, or a single bond, and in each1,4-phenylene group in the formula, any hydrogen atom is optionallysubstituted with a fluorine atom).
 18. The liquid crystal display deviceaccording to claim 17, wherein in General Formula (V), C represents asingle bond, and Z¹ represents a single bond.